Trip ideas from Chicago

171 places from Chicago with a recent return price. Prices we can stand behind come first, then the cheapest.

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Show all 30 places with recent prices from Chicago

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

City	From	Dates	Airports	Stops	Found
Orlando ORL	$263	1 Mar 2027 – 8 Mar 2027 · 7 nights	RFD → SFB	out nonstop, back nonstop	found 2 days ago	See prices for these dates
Houston HOU	$284	27 Mar 2027 – 4 Apr 2027 · 8 nights	ORD → IAH	out nonstop, back nonstop	found 3 days ago	See prices for these dates
Fort Lauderdale FLL	$287	16 Mar 2027 – 24 Mar 2027 · 8 nights	ORD → FLL	out nonstop, back nonstop	found 2 days ago	See prices for these dates
Las Vegas LAS	$299	10 Mar 2027 – 15 Mar 2027 · 5 nights	ORD → LAS	out 1 stop, back nonstop	found 3 days ago	See prices for these dates
Mexico City MEX	$314	2 Mar 2027 – 12 Mar 2027 · 10 nights	ORD → MEX	out nonstop, back nonstop	found 2 days ago	See prices for these dates
Cancun CUN	$409	11 Mar 2027 – 18 Mar 2027 · 7 nights	ORD → CUN	out 1 stop, back 1 stop	found 2 days ago	See prices for these dates

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