Trip ideas from Chicago

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

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Show all 18 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	$280	3 Apr 2027 – 10 Apr 2027 · 7 nights	RFD → SFB	out nonstop, back 1 stop	found 2 days ago	See prices for these dates
Tampa TPA	$317	18 Apr 2027 – 26 Apr 2027 · 8 nights	RFD → TPA	out 1 stop, back nonstop	found 2 days ago	See prices for these dates
San Francisco SFO	$378	15 Apr 2027 – 17 Apr 2027 · 2 nights	ORD → SFO	out 1 stop, back 1 stop	found 2 days ago	See prices for these dates
Cancun CUN	$399	3 Apr 2027 – 17 Apr 2027 · 14 nights	ORD → CUN	out 1 stop, back 1 stop	found 2 days ago	See prices for these dates
Oakland OAK	$429	14 Apr 2027 – 17 Apr 2027 · 3 nights	MDW → OAK	out nonstop, back nonstop	found 2 days ago	See prices for these dates
Miami MIA	$482	4 Apr 2027 – 12 Apr 2027 · 8 nights	MDW → MIA	out 1 stop, back nonstop	found 3 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