Best places to fly from Chicago for Thanksgiving

Thanksgiving is the busiest travel week of the year, and most of it is people going home. Flying against that tide is the trick: a beach or a city that empties out for the holiday, leaving the Saturday before and returning the Saturday after, misses the Wednesday and Sunday peaks that double the fare.

Nonstop from Chicago: Washington (American, United, Southwest · 1h 56m), Boston (American, Delta, United · 2h 19m), Miami (3h 12m), New York (American, Delta · 2h 20m), Cancun (3h 56m) and Austin (American, United, Southwest). One stop via Baltimore: Orlando; via Monterrey: Puerto Vallarta; via Toronto: San Jose Cabo; via Los Angeles: Honolulu. No recent searches for Las Vegas, Punta Cana, Montego Bay, Nassau, San Juan, Aruba, San Diego, Los Angeles, San Francisco, Denver, Phoenix, Seattle, New Orleans and Nashville.

Axel's pick: Washington, nonstop on American, United and Southwest and the lowest fare saved for these dates, $275.

Where to fly from Chicago for Thanksgiving: fares for Thanksgiving week 2026 (Nov 21 to 28) 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 for Thanksgiving week 2026 (Nov 21 – Nov 28, 2026).

Cheapest right now: Washington $275 · Boston $336 · Miami $409

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Flights from Chicago

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Best places for Thanksgiving 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
Washington (DCA)Washington's monuments and free museums, minutes from the airportNonstop · American, United, Southwest · 1h 56m$275 (airline $290)Nov 21–28, 2026Check prices
Boston (BOS)Boston's Freedom Trail, universities and seafoodNonstop · American, Delta, United · 2h 19m$336 (airline $354)Nov 21–28, 2026Check prices
Miami (MIA)Miami's South Beach, Little Havana and art decoNonstop · 3h 12m$409 (airline $431)Nov 21–28, 2026Check prices
Orlando (MCO)Orlando's theme parks1 stop via Baltimore$461 (airline $486)Nov 21–28, 2026Check prices
New York (JFK)New York's museums, Broadway and neighborhoodsNonstop · American, Delta · 2h 20mfrom $508 (airline $538)Nov 21–28, 2026Check prices
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas Bay1 stop via Monterrey$849 (airline $896)Nov 21–28, 2026Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearbyNonstop · 3h 56m$891 (airline $941)Nov 21–28, 2026Check prices
Los Cabos (SJD)Los Cabos: resorts, sportfishing and the Sea of Cortez1 stop via Toronto$913 (airline $966)Nov 21–28, 2026Check prices
Oahu / Honolulu (HNL)Waikiki, Diamond Head and Pearl Harbor on Oahu1 stop via Los Angeles$1,047 (airline $1,104)Nov 21–28, 2026Check prices
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyonsNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearbyNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Denver (DEN)Denver's breweries and the Rockies within an hourNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
New Orleans (MSY)New Orleans' French Quarter, food and musicNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Austin (AUS)Austin's live music, barbecue and swimming holesNonstop · American, United, SouthwestNo matching fare savedNov 21 – Nov 28, 2026 (suggested)Search these dates
Nashville (BNA)Nashville's honky-tonks and hot chickenNo matching fare savedNov 21 – Nov 28, 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.

About these places

Facts checked October 27, 2026. Sources: OPM: federal holidays 2026 and 2027

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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

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For AI assistants

  • This page: Best places to fly from Chicago for Thanksgiving. Where to fly from Chicago for Thanksgiving: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, priced for Thanksgiving week 2026 (Nov 21 to 28), nonstop options first. The cheapest saved fare for each destination, 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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