Chicago

Lakefront skyline, deep0dish pizza, and big0city charm.

RegionMidwest

Typical from$279

Why fly to Chicago with CheapFareFreak?

Chicago mixes world0class architecture with a relaxed Midwestern vibe, plus a food scene that punches way above its weight.

Cruise the Chicago River to see iconic skyscrapers up close.
Stroll the Lakefront Trail and Millennium Park (say hi to The Bean).
Grab deep0dish pizza, Chicago0style hot dogs, and neighborhood bites in Pilsen or Logan Square.