This 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.
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.
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.
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.
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.
Waldorf Astoria Panama
Modern luxury in the Bella Vista district with a spa, outdoor pool, and upscale dining.
The Bristol Panama
Classic elegance in the financial district, known for outstanding service and refined rooms.
Don’t Leave Without Trying
Sancocho
A comforting chicken soup and national staple
Ropa Vieja
Slow-stewed shredded beef packed with flavor
Patacones
Crispy fried plantains, perfect as a snack or side
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.
The Flights
Fantastic find on this routing. The Bogota layover bonus is lowkey genius, basically turning a$288 fare into two destinations. I've done similiar layover hacks before and the free stopover always feels like you're gaming the system in the best way.