Cheapest places to fly from Chicago in August

August is Europe's most crowded month and the cheapest for Mexico, the Caribbean and the desert, which are hot. The last two weeks are the value for everything, as schools go back and fares fall.

Nonstop from Chicago: Austin (American, United, Southwest · 2h 43m), Aruba (United, American), Montego Bay (United, American, Southwest), Nassau (United, American), San Diego (Alaska, United, American), Boston (American, Delta, United) and Washington (American, United, Southwest). One stop via San Diego: San Francisco and Honolulu. No recent searches for Cancun, Las Vegas, Orlando, San Jose Cabo, Puerto Vallarta, Punta Cana, San Juan, Miami, Los Angeles, New York, Denver, Phoenix, Seattle, New Orleans and Nashville.

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 August: the cheapest saved round trips within August 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 Aug.

Cheapest right now: Austin $314 · San Francisco $346 · Aruba $570

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Flights from Chicago

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Cheapest places in August 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
Austin (AUS)Austin's live music, barbecue and swimming holesNonstop · American, United, Southwest · 2h 43m$314 (airline $331)Aug 7–14, 2027Check prices
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearby1 stop via San Diego$346 (airline $365)Aug 5–9, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNonstop · United, American$570 (airline $603)Aug 7–14, 2027Check prices
Oahu / Honolulu (HNL)Waikiki, Diamond Head and Pearl Harbor on Oahu1 stop via San Diego$643 (airline $680)Aug 7–14, 2027Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearbyNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyonsNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Orlando (MCO)Orlando's theme parksNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Los Cabos (SJD)Los Cabos: resorts, sportfishing and the Sea of CortezNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas BayNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNonstop · United, American, SouthwestNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNonstop · United, AmericanNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Miami (MIA)Miami's South Beach, Little Havana and art decoNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNonstop · Alaska, United, AmericanNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
New York (JFK)New York's museums, Broadway and neighborhoodsNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Boston (BOS)Boston's Freedom Trail, universities and seafoodNonstop · American, Delta, UnitedNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Denver (DEN)Denver's breweries and the Rockies within an hourNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Washington (DCA)Washington's monuments and free museums, minutes from the airportNonstop · American, United, SouthwestNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
New Orleans (MSY)New Orleans' French Quarter, food and musicNo matching fare savedAug 7 – Aug 14, 2027 (suggested)Search these dates
Nashville (BNA)Nashville's honky-tonks and hot chickenNo matching fare savedAug 7 – Aug 14, 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 August. Where to fly from Chicago in August: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within August, 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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