Cheap Christmas and winter break flights from Chicago

Christmas and winter break 2026: the cheapest round trips from Chicago that travelers found recently, leaving December 12 to December 24 and coming back December 26 to January 6, with a carry-on counted in.

The cheapest is Fort Lauderdale for $233, Thu, Dec 24 to Mon, Dec 28 on Southwest.

Live prices to Fort Lauderdale for those dates

$233Cheapest round trip, carry-on included (est.)

22Places with fares for these dates

$233Cheapest in the US: Fort Lauderdale

$644Cheapest abroad: Mexico City

Places to stay in Fort Lauderdale

Hotels and rentals in Fort Lauderdale for Thu, Dec 24 to Mon, Dec 28, with current prices on a map you can move around.

See places to stay

Real hotels and rentals from Stay22's booking partners. Dipt may earn a commission when you book.

Need a car in Fort Lauderdale?

Rental cars at Fort Lauderdale Airport (FLL) for Thu, Dec 24 to Mon, Dec 28, compared across rental companies by QEEQ.

Cars for drivers 25+ Cars for drivers 21–24

Under 25? Most rental companies add a young driver fee, often $20 to $50 a day, and the 21–24 button shows prices with it in. Some memberships waive it, like AAA at Hertz for ages 20 to 24. Under 21, few companies rent at all. Dipt may earn a commission.

Cheapest Christmas and winter break trips from Chicago

Where	Leave	Return	Airline	Stops	Total, carry-on incl.	Live prices	Places to stay	Rental cars
Fort Lauderdale	Thu, Dec 24	Mon, Dec 28	Southwest	1 stop	$233	Live price	Stays	Car
Denver	Tue, Dec 22	Mon, Dec 28	Frontier	Nonstop	$272	Live price	Stays	Car
Houston	Wed, Dec 23	Wed, Dec 30	Frontier	1 stop	$321	Live price	Stays	Car
Atlanta	Wed, Dec 23	Sun, Dec 27	Frontier	Nonstop	$321	Live price	Stays	Car
Las Vegas	Wed, Dec 23	Sat, Dec 26	Frontier	Nonstop	$337	Live price	Stays	Car
Miami	Sun, Dec 20	Sat, Dec 26	Frontier	1 stop	$351	Live price	Stays	Car
San Antonio	Wed, Dec 23	Wed, Dec 30	Frontier	1 stop	$394	Live price	Stays	Car
San Diego	Thu, Dec 17	Sun, Dec 27	Frontier	1 stop	$419	Live price	Stays	Car
Sarasota	Thu, Dec 24	Fri, Jan 1	Southwest	1 stop	$424	Live price	Stays	Car
San Francisco	Tue, Dec 22	Sat, Dec 26	Frontier	1 stop	$447	Live price	Stays

Flying home? Every city, A to Z

The cheapest round trip from Chicago to each city with a fare for these dates.

Where	Leave	Return	Airline	Stops	Total, carry-on incl.	Live prices	Places to stay	Rental cars
Atlanta	Wed, Dec 23	Sun, Dec 27	Frontier	Nonstop	$321	Live price	Stays	Car
Cairo, Egypt	Sun, Dec 20	Sat, Jan 2	LOT	2 stops	$2,377	Live price	Stays	Car
Denver	Tue, Dec 22	Mon, Dec 28	Frontier	Nonstop	$272	Live price	Stays	Car
Fort Lauderdale	Thu, Dec 24	Mon, Dec 28	Southwest	1 stop	$233	Live price	Stays	Car
Guadalajara, Mexico	Sun, Dec 20	Sun, Dec 27	Frontier	3 stops	$783	Live price	Stays	Car
Houston	Wed, Dec 23	Wed, Dec 30	Frontier	1 stop	$321	Live price	Stays	Car
Istanbul, Türkiye	Tue, Dec 15	Mon, Jan 4	United	4 stops	$1,460	Live price	Stays
Las Vegas	Wed, Dec 23	Sat, Dec 26	Frontier	Nonstop	$337	Live price	Stays	Car
Lima, Peru	Fri, Dec 18	Fri, Jan 1	Frontier	3 stops	$1,336	Live price	Stays	Car
London, UK	Wed, Dec 23	Mon, Jan 4	JetBlue	1 stop	$736	Live price	Stays
Medellín, Colombia	Sun, Dec 20	Sat, Dec 26	Frontier	2 stops	$986	Live price	Stays
Mexico City, Mexico	Fri, Dec 18	Sat, Dec 26	American Airlines	2 stops	$644	Live price	Stays
Miami	Sun, Dec 20	Sat, Dec 26	Frontier	1 stop	$351	Live price	Stays	Car
Montego Bay, Jamaica	Tue, Dec 22	Wed, Dec 30	American Airlines	2 stops	$873	Live price	Stays	Car
Nairobi, Kenya	Thu, Dec 24	Sun, Jan 3	Qatar Airways	2 stops	$2,224	Live price	Stays	Car
San Antonio	Wed, Dec 23	Wed, Dec 30	Frontier	1 stop	$394	Live price	Stays	Car
San Diego	Thu, Dec 17	Sun, Dec 27	Frontier	1 stop	$419	Live price	Stays	Car
San Francisco	Tue, Dec 22	Sat, Dec 26	Frontier	1 stop	$447	Live price	Stays
San Juan, Puerto Rico	Wed, Dec 16	Wed, Dec 30	Frontier	2 stops	$562	Live price	Stays	Car
Sarasota	Thu, Dec 24	Fri, Jan 1	Southwest	1 stop	$424	Live price	Stays	Car
Seoul, South Korea	Tue, Dec 15	Tue, Dec 29	Icelandair	3 stops	$1,792	Live price	Stays
Tokyo, Japan	Mon, Dec 21	Mon, Jan 4	United	1 stop	$2,443	Live price	Stays

Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast, especially around the holidays: check the live price before you book.

Questions about Christmas and winter break flights from Chicago

What's the cheapest place to fly from Chicago for Christmas?

Of the fares travelers found recently, the cheapest round trips with a carry-on are Fort Lauderdale ($233, Thu, Dec 24 to Mon, Dec 28), Denver ($272, Tue, Dec 22 to Mon, Dec 28) and Houston ($321, Wed, Dec 23 to Wed, Dec 30).

What day should I fly for Christmas?

Of the cheapest trips found from Chicago, more leave on Wednesday, December 23 than any other day. Flexible? Check live prices a day or two either side: around the holidays, one day can change the price a lot.

Do these prices include bags?

They include a carry-on both ways, using our estimate of each airline's fee. A checked bag usually costs extra (bringing gifts? add that to the price), even on long flights abroad on the cheapest fares, though some airlines like Emirates include one.

How these prices work

These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).

Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.