Cheapest places to fly from Chicago in January

January after the first week is the cheapest month to fly to the beach and to Europe alike: the holiday crowds gone, fares at the year's low, and Mexico, the Caribbean and Hawaii in dry season. Ski towns are the one exception.

Nonstop from Chicago: Las Vegas (3h 55m), Seattle (Alaska, Delta, United · 4h 43m), Cancun (3h 57m), Nassau (United, American · 3h 23m), Honolulu (United, American · 9h 28m), Montego Bay (United, American, Southwest), Aruba (United, American), Punta Cana (American, United, DM · 4h 37m), Los Angeles (American, Delta, United) and New York (American, Delta). One stop via Houston: Miami; via Atlanta: Austin and Orlando; via Orlando: Nashville; via Las Vegas: New Orleans; via Dallas: Denver; via Tampa: San Juan; via Guadalajara: San Jose Cabo; via Mexico City: Puerto Vallarta. No recent searches for San Diego, San Francisco, Boston, Phoenix and Washington.

Axel's pick: Las Vegas, nonstop and the lowest fare saved for these dates, $172.

Where to fly from Chicago in January: the cheapest saved round trips within January 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 Jan.

Cheapest right now: Miami $167 · Las Vegas $172 · Austin $182

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Flights from Chicago

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Cheapest places in January from other cities

Fares observed October 22 – 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
Miami (MIA)Miami's South Beach, Little Havana and art deco1 stop via Houston$167 (airline $176)Jan 13–15, 2027Check prices
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyonsNonstop · 3h 55m$172 (airline $182)Jan 23–26, 2027Check prices
Austin (AUS)Austin's live music, barbecue and swimming holes1 stop via Atlanta$182 (airline $192)Jan 9–23, 2027Check prices
Nashville (BNA)Nashville's honky-tonks and hot chicken1 stop via Orlando$188 (airline $198)Jan 9–23, 2027Check prices
New Orleans (MSY)New Orleans' French Quarter, food and music1 stop via Las Vegas$210 (airline $221)Jan 14–16, 2027Check prices
Denver (DEN)Denver's breweries and the Rockies within an hour1 stop via Dallas$214 (airline $226)Jan 15–18, 2027Check prices
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNonstop · Alaska, Delta, United · 4h 43m$237 (airline $250)Jan 9–16, 2027Check prices
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the US1 stop via Tampa$245 (airline $259)Jan 12–19, 2027Check prices
Orlando (MCO)Orlando's theme parks1 stop via Atlanta$294 (airline $310)Jan 1–3, 2027Check prices
Los Cabos (SJD)Los Cabos: resorts, sportfishing and the Sea of Cortez1 stop via Guadalajara$378 (airline $399)Jan 15–18, 2027Check prices
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas Bay1 stop via Mexico City$382 (airline $404)Jan 15–18, 2027Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearbyNonstop · 3h 57m$400 (airline $422)Jan 15–18, 2027Check prices
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNonstop · United, American · 3h 23m$464 (airline $490)Jan 12–19, 2027Check prices
Oahu / Honolulu (HNL)Waikiki, Diamond Head and Pearl Harbor on OahuNonstop · United, American · 9h 28m$485 (airline $512)Jan 12–19, 2027Check prices
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNonstop · United, American, Southwest$503 (airline $530)Jan 12–19, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNonstop · United, American$1,069 (airline $1,130) · 2 adultsJan 16–23, 2027Check prices
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNonstop · American, United, DM · 4h 37m$1,143 (airline $1,209) · 2 adultsJan 16–23, 2027Check prices
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNo matching fare savedJan 16 – Jan 23, 2027 (suggested)Search these dates
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNonstop · American, Delta, UnitedNo matching fare savedJan 16 – Jan 23, 2027 (suggested)Search these dates
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearbyNo matching fare savedJan 16 – Jan 23, 2027 (suggested)Search these dates
New York (JFK)New York's museums, Broadway and neighborhoodsNonstop · American, DeltaNo matching fare savedJan 16 – Jan 23, 2027 (suggested)Search these dates
Boston (BOS)Boston's Freedom Trail, universities and seafoodNo matching fare savedJan 16 – Jan 23, 2027 (suggested)Search these dates
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNo matching fare savedJan 16 – Jan 23, 2027 (suggested)Search these dates
Washington (DCA)Washington's monuments and free museums, minutes from the airportNo matching fare savedJan 16 – Jan 23, 2027 (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.

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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 January. Where to fly from Chicago in January: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within January, 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.
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