Cheapest places to fly from Chicago for a week

A week is the range of a nonstop to anywhere in the Americas or Hawaii, and the minimum for Europe from the East Coast. The Saturday-to-Saturday week is the one most fares are built around; midweek departures run cheaper.

Nonstop from Chicago: Denver (2h 52m), Phoenix (3h 47m), Nashville (United, American, Southwest · 1h 24m), Las Vegas (4h 23m), San Diego (4h 31m), New Orleans (United, Southwest, American), Washington (American, United, Southwest · 1h 44m), Los Angeles (4h 18m), Boston (Southwest, United, American · 2h 26m) and Austin (2h 43m), and 13 more. One stop via Denver: San Francisco.

Axel's pick: Denver, nonstop and the lowest fare saved for these dates, $55.

Where to fly from Chicago for a week: fares for 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.

The cheapest matching round trip we’ve seen recently for each destination.

Cheapest right now: Denver $55 · Phoenix $147 · Nashville $167

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Flights from Chicago

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Cheapest places for a week from other cities

Fares observed October 21 – 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 52m$55 (airline $58)Nov 10–17, 2026Check prices
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNonstop · 3h 47m$147 (airline $155)Dec 5–12, 2026Check prices
Nashville (BNA)Nashville's honky-tonks and hot chickenNonstop · United, American, Southwest · 1h 24m$167 (airline $176)Dec 8–15, 2026Check prices
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyonsNonstop · 4h 23m$184 (airline $195)Jan 9–16, 2027Check prices
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNonstop · 4h 31m$186 (airline $197)Dec 12–19, 2026Check prices
New Orleans (MSY)New Orleans' French Quarter, food and musicNonstop · United, Southwest, American$190 (airline $200)Jan 12–19, 2027Check prices
Washington (DCA)Washington's monuments and free museums, minutes from the airportNonstop · American, United, Southwest · 1h 44m$195 (airline $206)Jan 12–19, 2027Check prices
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNonstop · 4h 18m$207 (airline $219)Jan 9–16, 2027Check prices
Boston (BOS)Boston's Freedom Trail, universities and seafoodNonstop · Southwest, United, American · 2h 26m$209 (airline $220)Jan 9–16, 2027Check prices
Austin (AUS)Austin's live music, barbecue and swimming holesNonstop · 2h 43m$209 (airline $220)Nov 14–21, 2026Check prices
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearby1 stop via Denver$213 (airline $225)Dec 12–19, 2026Check prices
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNonstop · Alaska, Delta, United · 4h 33m$237 (airline $250)Jan 9–16, 2027Check prices
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNonstop · 4h 37m$245 (airline $259)Jan 12–19, 2027Check prices
Orlando (MCO)Orlando's theme parksNonstop · 2h 30m$248 (airline $262)Nov 30–Dec 6, 2026Check prices
New York (JFK)New York's museums, Broadway and neighborhoodsNonstop · American, Delta · 2h 24m$282 (airline $297)Jan 12–19, 2027Check prices
Los Cabos (SJD)Los Cabos: resorts, sportfishing and the Sea of CortezNonstop · American, United, Southwest$310 (airline $328)Jan 15–22, 2027Check prices
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas BayNonstop · 4h 38m$399 (airline $420)Jan 12–19, 2027Check prices
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNonstop · 4h 45m$413 (airline $437)Nov 10–17, 2026Check 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 · American, United · 9h 20m$485 (airline $512)Jan 12–19, 2027Check prices
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNonstop · United, American, Southwest · 4h 08m$503 (airline $530)Jan 12–19, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNonstop · American, United · 5h 12m$512 (airline $539)Jan 12–19, 2027Check prices
Miami (MIA)Miami's South Beach, Little Havana and art decoNonstop · 3h 16m$622 (airline $657)Dec 26, 2026–Jan 2, 2027Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearbyNonstop · 3h 44m$2,601 (airline $2,742)Jun 19–26, 2027Check prices

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 for a week. Where to fly from Chicago for a week: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, priced for , 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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