Direct Flights from Grand Rapids to Chicago for Just $77 Roundtrip!
You can now fly direct from Grand Rapids (GRR) to Chicago (MDW) on Southwest Airlines for as little as $77 roundtrip. Dates are available from October through January, making this the perfect time for a long weekend in the Windy City. This route is usually $200+ so this is a great price for a long weekend in Chicago.
🏙 Why Midway is Perfect for a Weekend Stay
Chicago’s Midway International Airport (MDW) is ideal for short trips. It’s smaller and easier to navigate than O’Hare, and just 25 minutes from downtown on the Orange Line train. That means less travel hassle and more time to enjoy the city.
🎉 Things to Do on a Chicago Long Weekend
Millennium Park & The Bean – iconic photo spot and great for a city stroll.
Art Institute of Chicago – one of the world’s great art museums.
Chicago River Architecture Cruise – a must for skyline views and history.
Magnificent Mile – shopping, dining, and architectural landmarks.
Neighborhoods – explore Pilsen for murals and tacos, or Wicker Park for boutiques and coffee shops.
Comedy & Jazz – catch a show at The Second City or a late-night jazz club.
Museum Campus – visit the Field Museum, Shedd Aquarium, or Adler Planetarium.
Food – deep dish pizza, Chicago hot dogs, and Fulton Market’s restaurant scene.
🎄 Special Holiday Highlights
If you travel during the Christmas season, Chicago shines with festive events:
Christkindlmarket – a German-inspired holiday market at Daley Plaza.
ZooLights at Lincoln Park Zoo – a free holiday lights display.
Ice Skating at Millennium Park – skate beneath the skyline.
Holiday shopping on Michigan Avenue – the Magnificent Mile lit up for the season.
Navy Pier’s Winter WonderFest – indoor rides and holiday cheer for families.
🏆 Why This Deal is Worth It
At only $77 roundtrip, these flights are cheaper than driving and parking. With easy access from Midway, you’ll maximize your weekend and make the most of your time in Chicago, whether for a crisp fall getaway or a magical holiday trip.
The Flights
