Cheapest places to fly from Chicago in February

February is dry season on every warm coast and the best weather of the year in Mexico and the Caribbean, with Presidents' Day week the one expensive stretch. Europe and the big US cities are in low season and cheap.

Nonstop from Chicago: Phoenix (3h 56m), San Diego (4h 20m), New Orleans (2h 33m), Aruba (5h 12m), Cancun (3h 45m), Puerto Vallarta (4h 38m), San Jose Cabo (4h 45m), Punta Cana (4h 34m), Honolulu (9h 20m) and New York (American, Delta), and 3 more. One stop via Panama City: Montego Bay; via Charlotte: Nassau. No recent searches for Las Vegas, Orlando, San Juan, Miami, Los Angeles, San Francisco, Denver, Seattle and Nashville.

Axel's pick: Phoenix, nonstop and the lowest fare saved for these dates, $246.

Where to fly from Chicago in February: the cheapest saved round trips within February 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 Feb.

Cheapest right now: Phoenix $246 · San Diego $286 · New Orleans $356

Search my own dates and travelers

Flights from Chicago

More trip ideas from Chicago

Cheapest places in February 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
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNonstop · 3h 56m$246 (airline $260)Feb 10–15, 2027Check prices
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNonstop · 4h 20m$286 (airline $302)Feb 12–15, 2027Check prices
New Orleans (MSY)New Orleans' French Quarter, food and musicNonstop · 2h 33m$356 (airline $375)Feb 5–10, 2027Check prices
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and Negril1 stop via Panama City$475 (airline $502)Feb 12–16, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNonstop · 5h 12m$547 (airline $577)Feb 12–16, 2027Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearbyNonstop · 3h 45m$570 (airline $603) · 2 adultsFeb 13–20, 2027Check prices
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas BayNonstop · 4h 38m$591 (airline $625) · 2 adultsFeb 13–20, 2027Check prices
Los Cabos (SJD)Los Cabos: resorts, sportfishing and the Sea of CortezNonstop · 4h 45m$601 (airline $636) · 2 adultsFeb 13–20, 2027Check prices
Nassau (NAS)Nassau and Paradise Island, a short flight from the East Coast1 stop via Charlotte$756 (airline $799) · 2 adultsFeb 13–20, 2027Check prices
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNonstop · 4h 34m$921 (airline $971) · 2 adultsFeb 13–20, 2027Check prices
Oahu / Honolulu (HNL)Waikiki, Diamond Head and Pearl Harbor on OahuNonstop · 9h 20m$1,067 (airline $1,124) · 1 adult · 1 childFeb 11–16, 2027Check prices
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyonsNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
Orlando (MCO)Orlando's theme parksNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
Miami (MIA)Miami's South Beach, Little Havana and art decoNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearbyNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
New York (JFK)New York's museums, Broadway and neighborhoodsNonstop · American, DeltaNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
Boston (BOS)Boston's Freedom Trail, universities and seafoodNonstop · American, Delta, UnitedNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
Denver (DEN)Denver's breweries and the Rockies within an hourNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
Washington (DCA)Washington's monuments and free museums, minutes from the airportNonstop · American, United, SouthwestNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
Austin (AUS)Austin's live music, barbecue and swimming holesNonstop · American, United, SouthwestNo matching fare savedFeb 13 – Feb 20, 2027 (suggested)Search these dates
Nashville (BNA)Nashville's honky-tonks and hot chickenNo matching fare savedFeb 13 – Feb 20, 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.

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