Chicago
Lakefront skyline, deep-dish pizza, and big-city charm.
Why fly to Chicago with CheapFareFreak?
Chicago mixes world-class architecture with a relaxed Midwestern vibe, plus a food scene that punches way above its weight.
Trip highlights
- Cruise the Chicago River to see iconic skyscrapers up close.
- Stroll the Lakefront Trail and Millennium Park (say hi to The Bean ).
- Grab deep-dish pizza, Chicago-style hot dogs, and neighborhood bites in Pilsen or Logan Square.