Where to fly cheaply from Chicago in December

Lowest round-trip fares from Chicago for departures in December found recently: 30 destinations — from $81

Departure: December 2026

Plan a multi-city route

You will continue to our partner's website to see live prices and book. mibilet does not sell tickets.

Cheapest destinations from Chicago in December

Round trip prices

CHI DEN
Denver
Depart10 Dec Return14 Dec
F9 Direct
$81 View deal
CHI MSP
Minneapolis
Depart23 Dec Return25 Dec
WN Direct
$118 View deal
CHI OKC
Oklahoma City
Depart22 Dec Return5 Jan
WN Direct
$134 View deal
CHI SRQ
Sarasota
Depart6 Dec Return21 Dec
G4 Direct
$139 View deal
CHI DFW
Dallas
Depart3 Dec Return7 Dec
F9 Direct
$142 View deal
CHI MIA
Miami
Depart31 Dec Return9 Jan
WN Direct
$148 View deal
CHI FLL
Fort Lauderdale
Depart31 Dec Return10 Jan
F9 Direct
$149 View deal
CHI NYC
New York
Depart31 Dec Return3 Jan
F9 1 stop(s)
$149 View deal
CHI LAS
Las Vegas
Depart3 Dec Return8 Dec
F9 Direct
$157 View deal
CHI ORL
Orlando
Depart12 Dec Return14 Dec
F9 1 stop(s)
$175 View deal
CHI BWI
Baltimore
Depart17 Dec Return17 Jan
F9 Direct
$179 View deal
CHI SAN
San Diego
Depart3 Dec Return10 Dec
F9 1 stop(s)
$190 View deal
CHI BNA
Nashville
Depart2 Dec Return5 Dec
WN Direct
$204 View deal
CHI GDL
Guadalajara
Depart1 Dec Return9 Dec
Y4 1 stop(s)
$206 View deal
CHI SJU
San Juan
Depart5 Dec Return14 Dec
F9 1 stop(s)
$215 View deal
CHI TPA
Tampa
Depart20 Dec Return29 Dec
F9 Direct
$216 View deal
CHI WAS
Washington
Depart17 Dec Return17 Jan
F9 1 stop(s)
$225 View deal
CHI YMQ
Montreal
Depart14 Dec Return16 Dec
PD 1 stop(s)
$257 View deal
CHI HOU
Houston
Depart24 Dec Return28 Dec
F9 1 stop(s)
$266 View deal
CHI MBJ
Montego Bay
Depart7 Dec Return14 Dec
AC 1 stop(s)
$266 View deal
CHI YVR
Vancouver
Depart14 Dec Return8 Jan
F9 1 stop(s)
$281 View deal
CHI BOS
Boston
Depart15 Dec Return16 Dec
B6 Direct
$312 View deal
CHI SFO
San Francisco
Depart23 Dec Return28 Dec
F9 1 stop(s)
$314 View deal
CHI YTO
Toronto
Depart4 Dec Return6 Dec
PD Direct
$315 View deal
CHI PHL
Philadelphia
Depart28 Dec Return3 Jan
F9 Direct
$315 View deal
CHI MEX
Mexico City
Depart31 Dec Return15 Jan
F9 2 stop(s)
$329 View deal
CHI SLP
San Luis Potosi
Depart4 Dec Return10 Dec
F9 1 stop(s)
$336 View deal
CHI OAK
Oakland
Depart24 Dec Return28 Dec
WN Direct
$339 View deal
CHI LEX
Lexington
Depart11 Dec Return17 Dec
AA Direct
$341 View deal
CHI SJC
San Jose
Depart24 Dec Return28 Dec
AS 1 stop(s)
$350 View deal

Flight destinations

Flying from Chicago in December

This page shows where it is cheapest to fly from Chicago in December. Above are the lowest round-trip fares for departures that month that our partner services found recently, sorted by price. The list changes as people search, so check it again closer to your dates.

The cheapest destination in December in recent searches is Denver, from $81.

Fares change with the season, the day of the week and how far ahead you book. Check neighbouring dates in the price calendar and confirm the final price on the partner’s website: mibilet does not sell tickets and adds nothing to the price.

Frequently asked questions

Where can I fly cheaply from Chicago in December?
In recent searches the lowest round-trip fares from Chicago for departures in December were: Denver — $81, Minneapolis — $118, Oklahoma City — $134, Sarasota — $139, Dallas — $142. This is not a guaranteed fare: the final price is shown on the partner’s website before payment.
Can I buy the ticket on mibilet?
No. mibilet compares offers and sends you to the partner's website, where you book and pay. Check the fare rules, baggage allowance and total price there.