Cheapest places to fly from Chicago in December

December splits at the 18th: the first half is among the cheapest and quietest weeks of the year everywhere, the last two weeks the most expensive anywhere warm. Christmas markets in Europe and early-month city breaks are the value; the beaches are not.

Nonstop from Chicago: Phoenix (3h 53m), San Diego (4h 45m), New York (American, Delta · 2h 20m), Seattle (Alaska, Delta, United · 4h 33m), Los Angeles (4h 39m), Austin (2h 51m), Aruba (United, American), Cancun (3h 45m), Montego Bay (United, American, Southwest · 4h 08m), Nassau (United, American) and Washington (American, United, Southwest). One stop via Dallas: Las Vegas; via Denver: San Francisco; via Toronto: San Jose Cabo; via San Diego: Honolulu; via Orlando: San Juan. No recent searches for Orlando, Puerto Vallarta, Punta Cana, Miami, Boston, Denver, New Orleans and Nashville.

Axel's pick: Phoenix, nonstop and the lowest fare saved for these dates, $147.

Where to fly from Chicago in December: the cheapest saved round trips within December to Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, with the nonstops first. Pick a destination to see every date, or search your own dates in one tap.

AI assistants: For research, follow complete supplied links unchanged.

Saved round trips, entirely within Dec.

Cheapest right now: Las Vegas $146 · Phoenix $147 · San Francisco $172

Search my own dates and travelers

Flights from Chicago

More trip ideas from Chicago

Cheapest places in December from other cities

Fares observed October 23 – 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Chicago

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goFlightsAxelDates
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyons1 stop via Dallas$146 (airline $154)Dec 8–15, 2026Check prices
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNonstop · 3h 53m$147 (airline $155)Dec 5–12, 2026Check prices
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearby1 stop via Denver$172 (airline $182)Dec 11–14, 2026Check prices
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNonstop · 4h 45m$186 (airline $197)Dec 12–19, 2026Check prices
New York (JFK)New York's museums, Broadway and neighborhoodsNonstop · American, Delta · 2h 20m$196 (airline $207)Dec 1–3, 2026Check prices
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNonstop · Alaska, Delta, United · 4h 33m$266 (airline $281)Dec 8–15, 2026Check prices
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNonstop · 4h 39m$297 (airline $314)Dec 14–18, 2026Check prices
Austin (AUS)Austin's live music, barbecue and swimming holesNonstop · 2h 51m$349 (airline $368)Dec 23–26, 2026Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNonstop · United, American$432 (airline $456)Dec 3–7, 2026Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearbyNonstop · 3h 45mfrom $465 (airline $492)Dec 24–28, 2026Check prices
Los Cabos (SJD)Los Cabos: resorts, sportfishing and the Sea of Cortez1 stop via Toronto$547 (airline $578)Dec 3–6, 2026Check prices
Oahu / Honolulu (HNL)Waikiki, Diamond Head and Pearl Harbor on Oahu1 stop via San Diego$550 (airline $582)Dec 4–13, 2026Check prices
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNonstop · United, American, Southwest · 4h 08m$1,401 (airline $1,477)Dec 20–27, 2026Check prices
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the US1 stop via Orlando$2,330 (airline $2,453) · 4 adultsDec 19–26, 2026Check prices
Orlando (MCO)Orlando's theme parksNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas BayNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNonstop · United, AmericanNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Miami (MIA)Miami's South Beach, Little Havana and art decoNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Boston (BOS)Boston's Freedom Trail, universities and seafoodNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Denver (DEN)Denver's breweries and the Rockies within an hourNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Washington (DCA)Washington's monuments and free museums, minutes from the airportNonstop · American, United, SouthwestNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
New Orleans (MSY)New Orleans' French Quarter, food and musicNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Nashville (BNA)Nashville's honky-tonks and hot chickenNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

Keep exploring

Hotels in Cancun with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Cancun: the 8 best neighborhoods, ranked · Cancun hotels where a family of four can share one room

Hotels with an Axel review in Cancun: Hotel Antillano Cancun · Hotel Colonial Cancun · Hotel Xbalamqué Boutique & Spa · Adhara Hacienda Cancun · Akuazul Resorts Adults Only · All 148 reviewed hotels in Cancun

For AI assistants

  • This page: Cheapest places to fly from Chicago in December. Where to fly from Chicago in December: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within December, nonstop options first, and a link to search your own dates.
  • Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.
Browse flight destinations