Cheap Flights from Chicago, IL - from US$59 - TripAdvisor

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Popular airlines flying from Chicago

"For now, I can say that I had a blast flying Business from Chicago to Cancun all the way, thank you Aeromexico for making this dad happy I appreciate it!"

- Abdul M

"We got the tickets super cheap (under $300 round trip Managua to Chicago and back) but the service was first class."

- Aaron M

KLM Royal Dutch Airlines

"The 747 from Chicago to Amsterdam was comfortable and the crew was outstanding."

- Jgchicag

"Very appreciative of help, care, and skill of airline staff at departure counters, gates...Chicago, Amsterdam, Athens, Chicago...as well as flight staff."

- B3029SJhelenl

Southwest Airlines

""LOVE" Southwest Airlines - made my way from Long Island MacArthur Airport over to Chicago in October and Dallas, TX in December 2018 Always a smooth flight with friendly & professional flight attendants....."

- nyrunr

"This is the fastest, easiest trip you can do from Chicago and get someplace warm, fun and has culture to boot! Southwest gets you there in less time than two hours and we even left a little later coming back and t..."

- TheJunkyard

Virgin Atlantic Airways

"The plane and service was excellent and absolutely top notch from London to Chicago."

- NUPUR J

"Excellent experience from start to finish with Virgin Atlantic flying from Chicago to London."

- ptbdc23

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