Trip ideas from Chicago

117 places from Chicago with a recent one-way 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

89 hidden by travel month

Deals worth a look

Orlando
12 Jan 2027
Leaves from O'Hare International Airport (ORD) → MCO
From $75 one way
1 traveler · Economy
found yesterday
41.4% below the middle price here: the cheapest one-way fare on each of 9 departure dates is usually $102 to $135.
This trip has 1 stop.
See this trip Open this trip
Moscow
15 Jan 2027
Leaves from O'Hare International Airport (ORD) → VKO
From $574 one way
1 traveler · Economy
found yesterday
16.2% below the middle price here: the cheapest one-way fare on each of 10 departure dates is usually $606 to $778.
This trip has 3 stops.
See this trip Open this trip

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 28 places with recent prices from Chicago

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

City	From	Dates	Airports	Stops	Found
Fort Lauderdale FLL	$65	7 Jan 2027	ORD → FLL	nonstop	found yesterday	Open this trip
Orlando ORL	$75	12 Jan 2027	ORD → MCO	1 stop	found yesterday	Open this trip
Denver DEN	$80	26 Jan 2027	ORD → DEN	nonstop	found 4 days ago	Open this trip
San Juan SJU	$100	11 Jan 2027	ORD → SJU	nonstop	found 2 days ago	Open this trip
Los Angeles LAX	$104	7 Jan 2027	MDW → LAX	nonstop	found 5 days ago	Open this trip
Ontario ONT	$135	25 Jan 2027	ORD → ONT	1 stop	found yesterday	Open this trip
Knoxville TYS	$135

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

Trip ideas from Chicago

Narrow it down

Deals worth a look

Orlando

Moscow