Cheapest places to fly from Chicago in September

September is the best month to fly almost anywhere: Europe in its second summer at lower fares, the national parks quiet, the beaches warm and cheap, the big US cities back to life. Labor Day weekend is the only peak.

Nonstop from Chicago: Austin (American, United, Southwest · 2h 44m), Nashville (American, United, Southwest · 1h 24m), Denver (Southwest, American, Frontier · 2h 33m), San Diego (Southwest, American, Alaska · 4h 12m), Las Vegas (Southwest · 3h 53m), Seattle (Southwest, Delta, American · 4h 39m), Aruba (American, United), San Jose Cabo (American, United, Southwest), Punta Cana (Southwest, United, American) and Montego Bay (American, United, Southwest), and 6 more. No recent searches for Cancun, Orlando, Honolulu, Puerto Vallarta, San Juan, Miami, Los Angeles and Washington.

Axel's pick: Austin, nonstop on American, United and Southwest and the lowest fare saved for these dates, $314.

Where to fly from Chicago in September: the cheapest saved round trips within September 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, entirely within Sep.

Cheapest right now: Austin $314 · Nashville $346 · Denver $372

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Flights from Chicago

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Cheapest places in September from other cities

Fares observed October 24 – 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
Austin (AUS)Austin's live music, barbecue and swimming holesNonstop · American, United, Southwest · 2h 44m$314 (airline $331)Sep 11–18, 2027Check prices
Nashville (BNA)Nashville's honky-tonks and hot chickenNonstop · American, United, Southwest · 1h 24m$346 (airline $365)Sep 11–18, 2027Check prices
Denver (DEN)Denver's breweries and the Rockies within an hourNonstop · Southwest, American, Frontier · 2h 33m$372 (airline $393)Sep 3–6, 2027Check prices
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNonstop · Southwest, American, Alaska · 4h 12m$413 (airline $437)Sep 3–6, 2027Check prices
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyonsNonstop · Southwest · 3h 53m$433 (airline $457)Sep 3–6, 2027Check prices
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNonstop · Southwest, Delta, American · 4h 39m$444 (airline $469)Sep 3–6, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNonstop · American, United$545 (airline $575)Sep 11–18, 2027Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearbyNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Orlando (MCO)Orlando's theme parksNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Oahu / Honolulu (HNL)Waikiki, Diamond Head and Pearl Harbor on OahuNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Los Cabos (SJD)Los Cabos: resorts, sportfishing and the Sea of CortezNonstop · American, United, SouthwestNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas BayNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNonstop · Southwest, United, AmericanNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNonstop · American, United, SouthwestNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNonstop · United, AmericanNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Miami (MIA)Miami's South Beach, Little Havana and art decoNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearbyNonstop · American, United, SouthwestNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
New York (JFK)New York's museums, Broadway and neighborhoodsNonstop · American, DeltaNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Boston (BOS)Boston's Freedom Trail, universities and seafoodNonstop · Southwest, United, AmericanNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNonstop · SouthwestNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
Washington (DCA)Washington's monuments and free museums, minutes from the airportNo matching fare savedSep 11 – Sep 18, 2027 (suggested)Search these dates
New Orleans (MSY)New Orleans' French Quarter, food and musicNonstop · United, Southwest, AmericanNo matching fare savedSep 11 – Sep 18, 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 September. Where to fly from Chicago in September: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within September, 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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