Trip ideas from Chicago

108 places from Chicago with a recent one-way price. Prices we can stand behind come first, then the cheapest.

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Show all 20 places with recent prices from Chicago

The cheapest recent price for each place — per traveler in Economy.

City	From	Dates	Airports	Stops	Found
Tampa TPA	$84	3 Mar 2027	ORD → TPA	1 stop	found 2 days ago	Open this trip
Pittsburgh PIT	$150	5 Mar 2027	ORD → PIT	1 stop	found 2 days ago	Open this trip
Philadelphia PHL	$158	5 Mar 2027	ORD → PHL	nonstop	found 5 days ago	Open this trip
Phoenix PHX	$173	17 Mar 2027	ORD → PHX	nonstop	found 6 days ago	Open this trip
Boston BOS	$179	24 Mar 2027	ORD → BOS	nonstop	found 6 days ago	Open this trip
New York NYC	$181	24 Mar 2027	MDW → LGA	nonstop	found 6 days ago	Open this trip
Newburgh SWF	$247	3 Mar 2027	RFD → SWF	1 stop	found 6 days ago	Open this trip

Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work