Trip ideas from Chicago

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

Fly from somewhere else

Type a city or airport to see trip ideas.

Narrow it down

113 hidden by travel month

Deals worth a look

Nothing stands out strongly right now. Browse everything we can see, or keep looking.

FareTell may earn a commission when you book through a partner.

Map

The map isn't ready yet. Everything is in the list.

Show all 59 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	$179	16 Jan 2027 – 21 Jan 2027 · 5 nights	MDW → TPA	out 1 stop, back 1 stop	found 3 days ago	See prices for these dates
San Francisco SFO	$226	5 Jan 2027 – 13 Jan 2027 · 8 nights	ORD → SFO	out 2 stops, back 1 stop	found 2 days ago	See prices for these dates
Cancun CUN	$330	20 Jan 2027 – 30 Jan 2027 · 10 nights	ORD → CUN	out 1 stop, back 1 stop	found 3 days ago	See prices for these dates
San Jose SJO	$438	5 Jan 2027 – 11 Jan 2027 · 6 nights	ORD → SJO	out 1 stop, back 1 stop	found 3 days ago	See prices for these dates
Reykjavik REK	$501	12 Jan 2027 – 19 Jan 2027 · 7 nights	ORD → KEF	out nonstop, back nonstop	found 2 days ago	See prices for these dates
Honolulu HNL	$524	5 Jan 2027 – 12 Jan 2027 · 7 nights	ORD → HNL	out 1 stop, back 1 stop	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