<![CDATA[Great Lakes Travel Deals: Illinois - Chicago (O'Hare / Midway)]]>https://www.greatlakestraveldeals.com/s/chicago-ohare-international-airporthttps://substackcdn.com/image/fetch/$s_!WtkB!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd60eb3a1-9a5d-41c5-a953-ec76f8307c76_1200x1200.pngGreat Lakes Travel Deals: Illinois - Chicago (O'Hare / Midway)https://www.greatlakestraveldeals.com/s/chicago-ohare-international-airportSubstackWed, 29 Apr 2026 16:44:37 GMT<![CDATA[Rare Find: $368 Chicago to Dubrovnik (Early May)!]]>https://www.greatlakestraveldeals.com/p/rare-find-368-chicago-to-dubrovnikhttps://www.greatlakestraveldeals.com/p/rare-find-368-chicago-to-dubrovnikSat, 04 Apr 2026 12:17:03 GMTIf you’ve been waiting for a shot at Europe this spring, this is one of those deals that makes you stop what you’re doing.

I found a flight from Chicago to Dubrovnik for just $368 round trip for travel in early May.

That’s not just a good deal—it’s likely a mistake fare.

This route typically runs $700+, and what really stands out is that the surrounding dates are still pricing in the $700–$750 range, which makes this one-off drop even more unusual.

Why this matters

  • ✔️ Less than half the normal price

  • ✔️ Peak shoulder-season timing in Croatia

  • ✔️ Extremely limited at this price point

Mistake fares like this don’t last long. Airlines can correct them at any time, and once a few people grab these seats, the lowest fares disappear quickly.

Why Dubrovnik?

Dubrovnik is one of the most visually striking coastal cities in Europe—think medieval walls, Adriatic views, and easy access to islands and boat days. Early May is a sweet spot with great weather, fewer crowds, and better pricing on hotels compared to summer.

If this fits your schedule, I wouldn’t overthink it—this is the kind of deal that’s usually gone by the time you circle back later in the day.

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]]><![CDATA[Chicago to Stockholm this Spring priced at $381!]]>https://www.greatlakestraveldeals.com/p/chicago-to-stockholm-this-springhttps://www.greatlakestraveldeals.com/p/chicago-to-stockholm-this-springMon, 09 Mar 2026 10:34:38 GMTHere’s a fun one for spring travel. Flights from Chicago to Stockholm are available starting at $381 round trip for travel in April through early May. Historically this route typically prices $550+, so this is a great price point.

One unique aspect of this deal:
• You’ll see the flight options using the link below, but you’ll need to take the travel times and locate the exact flights directly on Icelandair.com to book.

These itineraries include a 22-hour layover in Reykjavik, Iceland. The flights typically arrive in Iceland in the early evening and depart the following afternoon, which gives you plenty of time to enjoy dinner, breakfast, and a quick look around the city before continuing on to Chicago.

A few things travelers love doing in Stockholm in the spring:
• Gamla Stan (Old Town) – cobblestone streets, colorful buildings, and great cafes once the weather warms.
• Djurgården Island – perfect for walking or biking with museums like the Vasa Museum and ABBA Museum nearby.
• Stockholm Archipelago – spring boat trips start running again to the nearby islands.
• Outdoor cafés & waterfront walks – the city really comes alive once the long winter ends.

A cheap flight to Scandinavia plus a mini Iceland stopover is about as good of a spring travel combo as you’ll find.

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]]><![CDATA[Chicago to Auckland, New Zealand — $579 Roundtrip 🔥 (New Low!)]]>https://www.greatlakestraveldeals.com/p/chicago-to-auckland-new-zealand-579https://www.greatlakestraveldeals.com/p/chicago-to-auckland-new-zealand-579Wed, 18 Feb 2026 12:19:53 GMTThis is a big one.

Roundtrip flights from Chicago to Auckland are pricing at a rock-bottom $579 for travel in late February and early March. Historically, this route runs $1,200+, and until now the best I had seen was $766 (Dec 2025) and $882 (Oct 2023).

At $579, this is a true new low for one of the most bucket-list long-haul destinations in the world.

Yes — it’s short notice. But if you’ve got flexibility, remote work options, or a freshly reloaded vacation balance… this is how you visit a world-class country at a deep discount.

What To Do With 7–9 Days in New Zealand

If I had a week (or nine days), here’s how I’d structure it:

Auckland + Waiheke Island (2–3 days)

Harbor views, volcanic cones, waterfront dining, and an easy ferry to Waiheke for vineyards and coastal hikes.

Rotorua (1–2 days)

Geothermal parks, bubbling mud pools, Māori cultural experiences, and natural hot springs.

Queenstown (3–4 days)

Fly south. This is the adventure capital of the world — alpine lakes, dramatic mountains, Milford Sound day trip, hiking, wine country, or just soaking in the scenery.

Optional Add-On: Hobbiton (near Matamata) if you’re a LOTR fan — surprisingly fun even if you’re not.

Late February and early March is late summer in New Zealand — long daylight hours, warm temps, and shoulder-season value.

It’s rare to see a destination this far away price like a domestic long weekend.
If New Zealand is on your list… this is the kind of fare that can make it real. 🌏✈️

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]]><![CDATA[Incredible $46 Roundtrip Flights from Chicago to Florida!]]>https://www.greatlakestraveldeals.com/p/incredible-46-roundtrip-flights-fromhttps://www.greatlakestraveldeals.com/p/incredible-46-roundtrip-flights-fromThu, 12 Feb 2026 11:45:15 GMTHere are a few deeply discounted Saturday-to-Saturday flights from Chicago to Orlando, Fort Myers, and Fort Lauderdale that are now available starting at just $46 roundtrip for travel in April and May. That’s an incredible value for peak sunshine season, especially for clean one-week getaways that run Saturday to Saturday.

These fares are about as low as it gets and open the door to three of Florida’s most sought-after destinations without breaking the budget. Whether you’re planning a family spring break, a couples escape, or just need a reset from Midwest weather, this is one of the cheapest ways to lock in a full week in the sun.

Why visit? Orlando delivers world-class theme parks and family fun, Fort Myers offers Gulf Coast beaches and laid-back island vibes, and Fort Lauderdale blends boating culture, nightlife, and beautiful Atlantic shoreline into one easy-to-love coastal city.

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]]><![CDATA[Chicago to Key West for $177 on Delta!]]>https://www.greatlakestraveldeals.com/p/chicago-to-key-west-for-177-on-deltahttps://www.greatlakestraveldeals.com/p/chicago-to-key-west-for-177-on-deltaFri, 06 Feb 2026 11:49:10 GMTDelta has roundtrip flights from Chicago to Key West priced at just $177 for travel March through May, and then again August through December. That’s an incredible fare for a route that almost never dips this low — the only time I’ve seen it cheaper was back in May of 2023, when it briefly hit $175.

Key West is one of those destinations that feels like a true escape without needing a passport. Visitors love wandering Duval Street, catching the sunset celebration at Mallory Square, snorkeling and boating in crystal-clear waters, and soaking up the laid-back island vibe that makes everything slow down a notch.

One major highlight: Dry Tortugas National Park. Located about 70 miles west of Key West, it’s home to Fort Jefferson, turquoise water, and some of the best snorkeling in Florida. It’s one of the most unique national parks in the U.S. and absolutely worth the boat or seaplane trip.

At $177 roundtrip on Delta, this is one of the best opportunities you’ll see to get to Key West in 2025 — whether you’re chasing spring sunshine or planning a late-season island escape.

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]]><![CDATA[Chicago to Panama City, Panama - Flights from $288 Roundtrip (New Low)]]>https://www.greatlakestraveldeals.com/p/chicago-to-panama-city-panama-flightshttps://www.greatlakestraveldeals.com/p/chicago-to-panama-city-panama-flightsSat, 31 Jan 2026 22:08:38 GMTThis one jumped off the page. Flights from Chicago to Panama City, Panama are now available starting at just $288 roundtrip for travel in February and March — a new low on a route that typically averages $550+.

Even better, some of these itineraries include a ~24-hour layover in Bogotá, Colombia, which is a huge bonus if you’re open to a little adventure. A full day in Bogotá gives you the chance to explore historic La Candelaria, ride the cable car up Monserrate for sweeping city views, visit the world-class Gold Museum, and enjoy Colombia’s incredible food and coffee scene — essentially turning this deal into a two-countries-for-the-price-of-one trip.

Panama itself may feel a little off the beaten path, but that’s part of the appeal. Located just south of Costa Rica, the country offers a rare mix of Caribbean and Pacific beaches, lush rainforests, coffee-growing highlands, and a modern, cosmopolitan capital city. Add in the world-famous Panama Canal, and you’ve got a destination that punches well above its weight. Travel + Leisure has consistently highlighted Panama as a top destination for adventurous travelers — and at this price, with a built-in Bogotá stop, it’s even harder to ignore.

About Avianca (What to Know)

Avianca is Colombia’s flag carrier and one of the oldest airlines in the world, with a large network throughout Central and South America. While many of their lowest fares are more “no-frills,” Avianca is a safe, reputable airline with modern aircraft and efficient connections through major hubs. If you’re comfortable pre-selecting seats and paying for bags if needed, it’s an excellent way to reach Latin America at a steep discount.

avianca - Corporate news

Must-See Highlights in Panama City

Casco Viejo

A UNESCO World Heritage Site and the historic heart of the city. Expect colorful colonial buildings, rooftop bars, lively plazas, and some of the best dining in Panama.

Casco Viejo | Panama City's Old Quarter - Panama Sovereign Realty

Panama Canal (Miraflores Locks)

One of the world’s greatest engineering feats. Watch massive cargo ships pass through the canal and learn how it reshaped global trade.

Miraflores Visitor Center - Visit Canal de Panamá

Ancon Hill

A short hike that rewards you with panoramic views of Panama City, the canal, and the Pacific Ocean — plus chances to spot wildlife along the way.

THINGS TO DO IN PANAMA: hike cerro ancon | vista cañas

Great Places to Stay

American Trade Hotel (Casco Viejo)

Historic charm meets boutique luxury, with a rooftop pool, jazz club, and prime location in the old quarter.

American Trade Hotel Panama | Panama Luxury Hotel | casco antiguo hotels | Boutique Hotel in Casco Viejo Panama | Hotels in Panama City Panama

Waldorf Astoria Panama

Modern luxury in the Bella Vista district with a spa, outdoor pool, and upscale dining.

Waldorf Astoria Panama, Panama City, Panama

The Bristol Panama

Classic elegance in the financial district, known for outstanding service and refined rooms.

The Bristol Panama City, Panama City : Five Star Alliance

Don’t Leave Without Trying

Sancocho

A comforting chicken soup and national staple

Panamanian Sancocho Recipe | centralamerica.com

Ropa Vieja

Slow-stewed shredded beef packed with flavor

Ropa Vieja

Patacones

Crispy fried plantains, perfect as a snack or side

Patacones: Fried Green Plantains

With Chicago–Panama City flights starting at just $288, this is one of the best values we’ve seen for Central America. If you’ve been craving warm weather, culture, history, and adventure — Panama delivers, and this price makes it even sweeter.

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]]><![CDATA[Chicago to Honolulu Starting at $342 for Travel in February and March!]]>https://www.greatlakestraveldeals.com/p/chicago-to-honolulu-starting-at-342https://www.greatlakestraveldeals.com/p/chicago-to-honolulu-starting-at-342Fri, 30 Jan 2026 11:40:08 GMTAs you know…. Especially right now…. Winter in the Midwest can be a grind, so seeing flights from Chicago to Honolulu starting at $342 round trip definitely grabbed my attention. This route is normally $550+, so this is a rare chance to trade snow boots for sandals and squeeze in a serious winter warm-up at a deep discount. Availability is limited to February and March, which is prime timing for escaping cold temps without peak summer crowds.

Why people love Honolulu:

• Perfect mix of beach + city – world-class beaches like Waikiki paired with great dining, shopping, and nightlife
• Unreal scenery – Diamond Head, lush hikes, waterfalls, and turquoise water everywhere you look
• Easy island access – simple day trips to the North Shore, Pearl Harbor, or snorkeling at Hanauma Bay
• Year-round sunshine – even “winter” in Hawaii feels pretty close to perfect

If you’ve been dreaming about Hawaii but waiting for prices to come back down, this is one of the better Chicago-to-Hawaii deals I’ve seen in a while. Perfect excuse to break up winter and come back recharged 🌺✈️

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]]><![CDATA[Chicago to the Faroe Islands for $418 Roundtrip — Including Spring Break!]]>https://www.greatlakestraveldeals.com/p/chicago-to-the-faroe-islands-forhttps://www.greatlakestraveldeals.com/p/chicago-to-the-faroe-islands-forWed, 21 Jan 2026 11:50:38 GMTFlights from Chicago to the Faroe Islands are currently just $418 roundtrip for April and May, an exceptional deal for one of Europe’s most remote and dramatic destinations. This route typically prices around $950+, making this nearly a 50% discount and a rare opportunity for Midwest travelers to reach the Faroes at a truly accessible price point. Spring is an ideal time to visit, with longer daylight hours, fewer crowds, and the islands beginning to turn lush and green after winter.

The Faroe Islands are known for jaw-dropping scenery — towering sea cliffs, waterfalls pouring straight into the Atlantic, quiet fjords, and storybook villages connected by tunnels and ferries. Travelers love the sense of isolation, peaceful roads, world-class hiking, and a surprisingly impressive food scene built around fresh seafood and local ingredients. If you’ve been looking for a spring trip that feels untouched, wild, and completely different from anywhere else in Europe, this deal makes the Faroe Islands suddenly within reach.

Three Interesting Facts About the Faroe Islands

Remote Archipelago

The Faroe Islands are a group of 18 volcanic islands located between Iceland and Norway in the North Atlantic Ocean. Despite their remote location, they boast some of the most dramatic and beautiful landscapes in the world.

Rich Birdlife

The Faroe Islands are home to a vast array of bird species, making it a paradise for birdwatchers. The islands are particularly known for their large populations of puffins, gannets, and fulmars.

Innovative Infrastructure

The islands are linked by a series of tunnels, bridges, and ferries, making travel between them remarkably convenient. The sub-sea tunnels, in particular, are engineering marvels, connecting even the most remote islands and enhancing accessibility for residents and tourists alike.

Top Things to Do in the Faroe Islands

Visit the Village of Gásadalur

Nestled in the mountains with breathtaking views over the ocean, Gásadalur is one of the most picturesque villages in the Faroe Islands. The scenic hike to the village offers stunning vistas, and the Gásadalur waterfall is a must-see.

Explore Tórshavn

The capital city of the Faroe Islands, Tórshavn, is one of the smallest capitals in the world. Explore its charming old town, Tinganes, with its narrow streets and traditional turf-roofed houses. Don’t miss the National Museum to learn about Faroese history and culture.

Hike to Lake Sørvágsvatn

Known as the “floating lake,” Sørvágsvatn is a stunning optical illusion where the lake appears to be suspended above the ocean. The hike to the lake offers panoramic views and a unique perspective of this natural wonder.

Birdwatching at Vestmanna Sea Cliffs

Take a boat tour to the Vestmanna Sea Cliffs, where you can see thousands of seabirds nesting on the steep cliffs. The dramatic landscapes and abundant wildlife make this an unforgettable experience.

Discover Mykines

The westernmost island of the Faroe Islands, Mykines, is known for its rich birdlife, including puffins and gannets. Enjoy hiking trails with breathtaking views and explore the quaint village of Mykines with its traditional Faroese houses.

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]]><![CDATA[Chicago to Kauai: Winter Flights for $336 Roundtrip!]]>https://www.greatlakestraveldeals.com/p/chicago-to-kauai-winter-flights-forhttps://www.greatlakestraveldeals.com/p/chicago-to-kauai-winter-flights-forMon, 05 Jan 2026 11:22:49 GMTFlights on American Airlines from Chicago to Kauai are showing up around $336 roundtrip for travel in January and February — a significant drop from the typical $450+ price point on this route. For Hawaii travel during peak winter months, that’s an exceptional fare.

January and February are especially appealing for Midwest travelers: fewer crowds than the holidays, excellent weather, and the perfect antidote to winter back home.

Why Kauai Is a Favorite for So Many Travelers

Kauai is often called the Garden Isle — and for good reason. It’s less built-up than some of the other Hawaiian islands and leans heavily into natural beauty.

Unmatched scenery
Think dramatic cliffs along the Nā Pali Coast, lush rainforests, waterfalls, and emerald-green valleys. Whether you’re hiking, driving, or just sitting on a beach, Kauai feels cinematic.

Relaxed, low-key island vibe
Kauai is ideal for travelers who want to slow down. Fewer high-rises, quieter beaches, and a more laid-back pace make it perfect for couples, families, and anyone looking to unplug.

Great mix of adventure and downtime
You can hike Waimea Canyon in the morning, snorkel or beach-hop in the afternoon, and still be back in time for sunset. It’s an island that rewards both exploring and doing absolutely nothing.

The takeaway

Winter flights to Hawaii under $350 from Chicago don’t come around often — especially to Kauai. If you’ve been waiting for the right price to make a winter escape happen, this is one of the better Kauai deals we’ve seen.

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]]><![CDATA[Chicago to Bozeman direct at $169 for travel in March and April!]]>https://www.greatlakestraveldeals.com/p/chicago-to-bozeman-direct-at-169https://www.greatlakestraveldeals.com/p/chicago-to-bozeman-direct-at-169Fri, 26 Dec 2025 18:08:50 GMTDirect flights from Chicago are popping up at $169 roundtrip for travel in March and April. This route usually runs quite a bit higher, especially once spring and summer demand starts to build.

Early spring is one of the best times to visit Bozeman if you like space, scenery, and flexibility.

A few reasons Bozeman should be on your radar:

• Spring skiing at Bridger Bowl and Big Sky — fewer people, longer days, and still plenty of snow
• Yellowstone nearby — quieter roads, active wildlife, and way less congestion than summer
• Hot springs season — Bozeman Hot Springs or a short drive to Chico Hot Springs hits different in cool weather
• Downtown Bozeman — good food, breweries, coffee shops, and a relaxed mountain town feel before peak season

This is the kind of trip where you can ski one day, soak the next, and still have time to explore town.

If Bozeman has been on your list, $169 nonstop from Chicago is a strong excuse to go.

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]]><![CDATA[Chicago to Vancouver Drops to $184 Roundtrip (Spring–Early Summer)]]>https://www.greatlakestraveldeals.com/p/chicago-to-vancouver-drops-to-184https://www.greatlakestraveldeals.com/p/chicago-to-vancouver-drops-to-184Wed, 17 Dec 2025 11:58:00 GMTThis is a great fare for one of the most scenic city-to-nature gateways in North America. Roundtrip flights from Chicago to Vancouver are currently available starting at $184 for travel April through June, a big drop from the usual $300+ you’ll typically see on this route.

Spring and early summer are an ideal time to visit Vancouver. The city is coming alive after winter, cherry blossoms line the streets in April, patios open up, and you still get snow-capped mountains as a backdrop. It’s one of those destinations where you can pair a great food scene with easy access to the outdoors.

Why Vancouver is worth the trip:

  • Stanley Park & the Seawall – One of the best urban parks in the world, perfect for biking or walking.

  • Granville Island – Food stalls, local shops, and great people-watching.

  • Grouse Mountain – Just minutes from downtown for views, hiking, and late-season snow.

  • Whistler – An easy day trip or overnight if you want alpine scenery.

  • Food scene – Incredible Asian cuisine, seafood, and coffee culture.

If you’ve been waiting for an excuse to visit Vancouver—or revisit it—$184 roundtrip from Chicago is a great reason to lock something in for spring or early summer.

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]]><![CDATA[CHICAGO TO AUCKLAND, NEW ZEALAND — $766 ROUND TRIP!]]>https://www.greatlakestraveldeals.com/p/chicago-to-auckland-new-zealand-766https://www.greatlakestraveldeals.com/p/chicago-to-auckland-new-zealand-766Wed, 10 Dec 2025 12:21:33 GMTFlights from Chicago to Auckland on Air Canada are now available priced at $766 round trip for travel in February and March — a massive price cut on a route that has averaged north of $1,300. If New Zealand has ever been on your travel radar, this is a great price point.

February and March are late summer in New Zealand: warm days, long daylight, and postcard-level scenery everywhere you turn. Auckland makes for a great base with more than enough to fill a week — and it’s the perfect jumping-off point for exploring the rest of the country.

Here are a few things you can build into your trip:

  • Ferry to Waiheke Island for beaches, wineries, and the best coastal views close to the city.

  • Hobbiton — an easy and surprisingly fun day trip, even if you’re not a huge LOTR fan.

  • Bay of Islands, north of Auckland, for clear water, dolphin tours, and laid-back beach towns.

  • Rotorua & Taupō, a few hours south, for geothermal pools, Māori culture, and adventure activities.

  • Quick flight to Queenstown if you want to add the South Island’s mountains and Milford Sound.

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]]><![CDATA[Rare Flight Opportunity: Chicago to Hawaii for $282!]]>https://www.greatlakestraveldeals.com/p/rare-flight-opportunity-chicago-tohttps://www.greatlakestraveldeals.com/p/rare-flight-opportunity-chicago-toThu, 04 Dec 2025 11:42:01 GMTSouthwest just dropped an unbelievable deal from Chicago Midway (MDW) to Kahului, Maui (OGG) — $282 roundtrip for travel in April and May. This route normally runs $600+, so finding a fare this low is a true outlier and one of the best Hawaii deals of the year. Spring is also one of the most comfortable times to visit Maui, with warm temperatures in the low 80s, lighter crowds, and perfect conditions for beaches, hiking, and sightseeing.

Once on the island, a few Maui favorites include:

Sunrise at Haleakalā National Park

Watch the sun rise above the clouds.

Snorkeling at Molokini Crater

Some of the clearest water in Hawaii.

Road to Hana

Waterfalls, coastal cliffs, and rainforests.

Whale watching (early April)

The tail end of peak season.

Wailea Beach

Calm water and an upscale resort area with great dining.

With prices this low and spring availability wide open, this is the perfect time to lock in a Maui getaway for a fraction of the usual cost.

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]]><![CDATA[Chicago to Tokyo for $675 Roundtrip — This Is a Wild Price!]]>https://www.greatlakestraveldeals.com/p/chicago-to-tokyo-for-675-roundtriphttps://www.greatlakestraveldeals.com/p/chicago-to-tokyo-for-675-roundtripTue, 18 Nov 2025 12:03:37 GMTThis one honestly surprised me. There are very limited flights from Chicago to Tokyo for $675 roundtrip on Air Canada for travel in December. For context, this route is usually $1,200+, and it’s not uncommon to see it push even higher during the winter.

If Japan has been on your radar, this is one of those “book first, figure the details out later” kind of prices.

A Simple 5-Day December Itinerary Around Tokyo

December is such an underrated time to be in Japan — clear skies, crisp air, holiday lights everywhere, and the crowds are way lighter than cherry blossom season. Here’s an easy 5-day plan if you grab this fare.

Day 1 — Shibuya + Shinjuku

Ease into the city:

  • Check out Shibuya Crossing and Shibuya Sky for the big rooftop views

  • Wander through Shinjuku’s Omoide Yokocho + Golden Gai

  • Warm up with a bowl of ramen (Ichiran or Afuri are great starters)

Day 2 — Tokyo Midtown Lights + Roppongi

December means the city goes all-in on holiday illuminations.

  • Walk through the Midtown and Roppongi light displays

  • Stop for coffee and dessert in Aoyama or Nogizaka

  • End the night at Tokyo Tower lit up for the holidays

Day 3 — Asakusa + Tokyo Skytree

A classic Tokyo day.

  • Visit Senso-ji, one of the most photogenic spots in the city

  • Snack your way down Nakamise Street

  • Head up Tokyo Skytree for big views of a winter skyline

Day 4 — Day Trip to Hakone or Kamakura

Your choice depending on the vibe:

  • Hakone: Hot springs, mountain air, and views of Mt. Fuji

  • Kamakura: Coastal temples, the Great Buddha, and easy hiking trails

Both are perfect December day trips — cool weather, fewer crowds, great photos.

Day 5 — Tsukiji Market + Ginza

A fun last day:

  • Fresh sushi and street snacks in Tsukiji

  • Explore Ginza’s holiday windows and shops

  • Pick up gifts and snacks inside Tokyo Station before heading home

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]]><![CDATA[Flights from Chicago to Santiago, Chile Starting at $504 Round Trip on United Airlines!]]>https://www.greatlakestraveldeals.com/p/flights-from-chicago-to-santiagohttps://www.greatlakestraveldeals.com/p/flights-from-chicago-to-santiagoMon, 10 Nov 2025 11:56:12 GMTIf you’ve ever dreamed of exploring South America, this is your chance — round-trip flights from Chicago (ORD) to Santiago, Chile are starting at just $504 on United Airlines for travel between November and March, including an option over Thanksgiving week.

This is an incredible deal, as this route typically costs $900 or more, making it one of the best values we’ve seen for reaching South America from Chicago.

☀️ Weather in Santiago (November–March)

These months mark spring through summer in the Southern Hemisphere, bringing warm, sunny, and dry weather ideal for outdoor exploration:

  • November: Highs in the mid-70s°F, mild and comfortable

  • December–February: Highs in the 80s–90s°F, perfect for sightseeing and vineyard tours

  • March: Highs in the 70s°F, with cooler evenings and fewer crowds

🌄 Why Travelers Love Santiago and Beyond

A stunning mountain backdrop: Santiago sits in a valley surrounded by the Andes Mountains — you can ski, hike, or simply enjoy the views from Cerro San Cristóbal.

Wine country within reach: The Maipo and Casablanca Valleys, just outside the city, are home to some of Chile’s most famous vineyards and tours.

Easy access to adventure: From Santiago, you’re just a couple of hours from the Pacific coast and the colorful port city of Valparaíso, or a short flight from Patagonia or Easter Island.

Culture, cuisine, and charm: Explore Santiago’s neighborhoods like Bellavista and Lastarria for art, music, and authentic Chilean food — including empanadas and pastel de choclo (corn pie).

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]]><![CDATA[Chicago to Eugene, Oregon — $185 Round Trip on Delta!]]>https://www.greatlakestraveldeals.com/p/chicago-to-eugene-oregon-185-roundhttps://www.greatlakestraveldeals.com/p/chicago-to-eugene-oregon-185-roundThu, 23 Oct 2025 10:54:19 GMTIf you’ve been waiting for an excuse to explore the Pacific Northwest, this is it.

Flights from Chicago to Eugene, Oregon are available for just $185 round trip on Delta for travel December through February — an incredible fare considering this route typically runs $350+. The only time it’s ever dipped lower was back in February 2023, when it briefly hit $175.

I’ve listed a few Saturday-to-Saturday examples below, but there are plenty of options for shorter stays or midweek travel as well.

🌲 Why Eugene Is Still Worth Visiting in Winter

Winter in Oregon brings a quieter, cozier version of the Pacific Northwest — fewer crowds, misty landscapes, and the kind of small-town charm that makes this area a hidden gem for travelers.

Eugene sits at the southern end of the Willamette Valley, surrounded by rolling vineyards, dense forests, and rivers that seem made for slow mornings and fresh air. It’s a college town with an outdoorsy soul — and it holds its own in the colder months.

🏔️ Things to Do Around Eugene in Winter

Explore the Willamette Valley Wine Country

Even in winter, the vineyards surrounding Eugene are beautiful. Many tasting rooms stay open year-round, offering fireside pours and cozy atmospheres — King Estate and Sweet Cheeks Winery are two standouts.

Visit Mount Pisgah Arboretum

A perfect spot for a crisp winter hike with family or friends. The trails wind through mossy oak forests, meadows, and along the Willamette River — bring a camera for the foggy valley views.

Facilities – Mount Pisgah Arboretum

Catch a Game or Stroll Through Campus

The University of Oregon gives the city its heartbeat. Take a walk around campus or catch a basketball game at Matthew Knight Arena to experience local energy in full swing.

Day Trip to the Oregon Coast

The coast is just an hour’s drive west, where you can explore Florence, Heceta Head Lighthouse, and the dramatic winter surf of the Pacific Ocean — moody skies make for great photos.

Drive into the Cascades

Head east for snow-dusted mountain views and trails near Oakridge or Salt Creek Falls — Oregon’s second-highest waterfall. It’s a taste of the Cascades without the crowds.

Downtown Eugene’s Market Scene

While the famous Saturday Market takes a winter pause, the 5th Street Public Market stays buzzing year-round with local shops, cafés, and Oregon-made gifts.

5th Street Public Market

💡 Why This Deal Matters

Flights under $200 round trip on Delta are extremely rare for this route. With mild weather, scenic day trips in every direction, and a mix of culture, food, and outdoor beauty, Eugene delivers great value — especially in the quieter winter months.

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]]><![CDATA[🔥 Frontier Airlines Launches $54 Winter Flight Sale — Dozens of Destinations!]]>https://www.greatlakestraveldeals.com/p/frontier-airlines-launches-54-winterhttps://www.greatlakestraveldeals.com/p/frontier-airlines-launches-54-winterWed, 22 Oct 2025 11:01:39 GMTIf you’ve been waiting for a sign to book your next warm-weather escape — this is it.

Frontier Airlines just launched a massive winter sale featuring direct round-trip flights for as low as $54 from Chicago to some of the most popular U.S. destinations.

🌎 Where You Can Fly

Frontier’s sale includes nonstop routes to:
Las Vegas, Phoenix, Austin, Houston, Denver, Washington DC, Philadelphia, Charlotte, Orlando, Nashville, Miami, Fort Myers, Tampa, and Atlanta.

There are too many deals to list individually, but fares at this price point are generally available for winter travel between December and February — perfect for a quick weekend getaway or mid-winter warm-up.

💰 Why This Sale Stands Out

These routes typically run $150–$200+ round trip, even on budget carriers. Frontier’s flash fares offer a rare chance to plan ahead, escape the Midwest chill, and stretch your travel dollars further.

Whether you’ve been dreaming of a weekend in Vegas, a family escape to Orlando, or a sunshine reset in Phoenix or Fort Myers, this sale makes it possible for less than the cost of dinner out.

🧭 How to Find These Deals on Google Flights

If you want to search or compare prices quickly, here’s how to uncover Frontier’s $54 round-trip fares:

  1. Go to Google Flights.

  2. In the departure box, type Chicago.

  3. Leave the destination box blank to explore all available cities.

  4. Leave the dates open for now — this lets Google show the cheapest options.

  5. Click “Explore” on the right side of the screen.

  6. A map will appear showing destinations and prices — zoom out to see more cities.

  7. Click any destination (like Phoenix or Orlando) to open flight details.

  8. Then click “Price Graph” to view all available dates and lowest fares.

  9. Adjust the length of your trip (usually 3–6 days works best) to find your ideal combo.

  10. Once you spot a $54 fare, note the dates and then book directly through Frontier’s website for the lowest total price.

This is one of Frontier’s biggest winter sales of the year, and it won’t last long.

If you’re craving sunshine, live music, or a change of scenery this winter — now’s the time to book.

]]><![CDATA[Chicago (Midway) → Phoenix — $54 Round Trip!]]>https://www.greatlakestraveldeals.com/p/chicago-midway-phoenix-54-round-triphttps://www.greatlakestraveldeals.com/p/chicago-midway-phoenix-54-round-tripTue, 14 Oct 2025 10:47:35 GMTThis is one of those rare finds that’s too good not to share — a direct flight from Chicago Midway to Phoenix for just $54 round trip!

There’s only one flight available at this price point, but it’s absolutely worth jumping on. The schedule works well even for Michigan travelers willing to make the drive to Chicago — easy departure and arrival times make this an ideal pre-winter getaway.

To put this in perspective, this route typically runs around $150–$200, and the only time I’ve seen it lower was back in September 2023, when I spotted it for $38 round trip.

☀️ Five Things to Do Around Phoenix

  1. Hike Camelback Mountain – Iconic desert views right in the city.

  2. Explore Old Town Scottsdale – Great mix of art, food, and southwestern charm.

  3. Visit Sedona (2 hours north) – Red rocks, scenic drives, and unforgettable sunsets.

  4. Experience the Grand Canyon (3.5 hours north) – One of the world’s most awe-inspiring landscapes, perfect for a day or overnight trip.

  5. See Horseshoe Bend (just beyond the Grand Canyon) – One of Arizona’s most photographed spots — breathtaking at sunrise or sunset.

If you’ve been craving sunshine, desert hikes, or poolside warmth before Michigan’s winter sets in, this is your sign — book it today. 🌵✈️

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]]><![CDATA[Chicago to Nashville — Halloween Weekend for $39 Round Trip!]]>https://www.greatlakestraveldeals.com/p/chicago-to-nashville-halloween-weekendhttps://www.greatlakestraveldeals.com/p/chicago-to-nashville-halloween-weekendThu, 09 Oct 2025 11:01:25 GMTf you’ve been waiting for a reason to sneak away this fall, this might be it. Flights from Chicago to Nashville are currently available for just $39 round trip, perfectly timed for Halloween weekend or a quick autumn getaway. That’s an incredible deal — well below the historical average of $130+ for this route.

Whether you’re headed down for the live music and neon lights of Broadway, a Titans game, or pumpkin-spiced everything at local coffee spots like Barista Parlor, Nashville delivers big fall vibes with small-town warmth.

Even better, there are several other dates through October and November available at or near this same $39 price point.

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]]><![CDATA[✈️ Chicago to New York for Just $49 Roundtrip — A Historic Low! 🗽]]>https://www.greatlakestraveldeals.com/p/chicago-to-new-york-for-just-49-roundtriphttps://www.greatlakestraveldeals.com/p/chicago-to-new-york-for-just-49-roundtripWed, 08 Oct 2025 10:43:13 GMTIf you’ve been waiting for an excuse to head to New York, this is it. Direct flights from Chicago to New York are now available starting at just $49 roundtrip for travel October through December — the lowest price we’ve recorded on this route.

This route has historically averaged $135+, so this is a fantastic savings and one of the best opportunities we’ve seen to visit the Big Apple before the holidays.

🍂 Why Now’s the Perfect Time to Go

  • Central Park in full fall color 🌳🍁

  • The Rockefeller Center tree lighting and early holiday markets 🎄

  • Broadway shows, rooftop views, and that unmistakable NYC energy ✨

Whether it’s a quick weekend getaway, a pre-holiday shopping trip, or a long-overdue visit with friends, this deal makes it easy to experience New York for less than dinner and a show.

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