Best places to fly from Chicago for Presidents' Day weekend

Presidents' Day weekend is the winter's big getaway: ski towns and warm beaches both peak, and fares rise for the Friday out and the Monday back. A city nobody associates with February, New Orleans, Austin, San Diego, is the value play.

Nonstop from Chicago: Denver (2h 51m), Orlando (2h 48m), Miami (3h 12m), Puerto Vallarta (4h 47m), Montego Bay (United, American, Southwest), Aruba (American, United · 5h 13m), Honolulu (American, United · 9h 23m), Nassau (United, American · 3h 32m), Punta Cana (United, American, DM) and San Diego (Alaska, United, American), and 6 more. One stop via Mexico City: San Jose Cabo; via Orlando: Cancun. No recent searches for Las Vegas, San Juan, San Francisco, Boston, New Orleans and Nashville.

Axel's pick: Denver, nonstop and the lowest fare saved for these dates, $174.

Where to fly from Chicago for Presidents' Day weekend: fares for Presidents' Day weekend 2027 (Feb 12 to 16) 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.

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Saved round trips for Presidents' Day weekend 2027 (Feb 12 – Feb 16, 2027).

Cheapest right now: Denver $174 · Orlando $252 · Miami $297

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Flights from Chicago

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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
Denver (DEN)Denver's breweries and the Rockies within an hourNonstop · 2h 51m$174 (airline $184)Feb 12–16, 2027Check prices
Orlando (MCO)Orlando's theme parksNonstop · 2h 48m$252 (airline $265)Feb 12–16, 2027Check prices
Miami (MIA)Miami's South Beach, Little Havana and art decoNonstop · 3h 12m$297 (airline $313)Feb 12–16, 2027Check prices
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas BayNonstop · 4h 47m$413 (airline $436)Feb 12–16, 2027Check prices
Los Cabos (SJD)Los Cabos: resorts, sportfishing and the Sea of Cortez1 stop via Mexico City$419 (airline $442)Feb 12–16, 2027Check prices
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNonstop · United, American, Southwest$475 (airline $502)Feb 12–16, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNonstop · American, United · 5h 13m$547 (airline $577)Feb 12–16, 2027Check prices
Oahu / Honolulu (HNL)Waikiki, Diamond Head and Pearl Harbor on OahuNonstop · American, United · 9h 23m$571 (airline $604)Feb 12–16, 2027Check prices
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNonstop · United, American · 3h 32m$588 (airline $620)Feb 12–16, 2027Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearby1 stop via Orlando$733 (airline $772)Feb 12–16, 2027Check prices
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyonsNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNonstop · United, American, DMNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNonstop · Alaska, United, AmericanNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNonstop · Southwest, American, UnitedNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearbyNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
New York (JFK)New York's museums, Broadway and neighborhoodsNonstop · American, DeltaNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Boston (BOS)Boston's Freedom Trail, universities and seafoodNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNonstop · Southwest, American, UnitedNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNonstop · Alaska, Delta, UnitedNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Washington (DCA)Washington's monuments and free museums, minutes from the airportNonstop · American, United, SouthwestNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
New Orleans (MSY)New Orleans' French Quarter, food and musicNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Austin (AUS)Austin's live music, barbecue and swimming holesNonstop · American, United, SouthwestNo matching fare savedFeb 12 – Feb 16, 2027 (suggested)Search these dates
Nashville (BNA)Nashville's honky-tonks and hot chickenNo matching fare savedFeb 12 – Feb 16, 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.

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

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

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  • This page: Best places to fly from Chicago for Presidents' Day weekend. Where to fly from Chicago for Presidents' Day weekend: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, priced for Presidents' Day weekend 2027 (Feb 12 to 16), 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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