Cheapest places to fly from Chicago in November

November is the cheapest month of the year to fly almost anywhere except Thanksgiving week: Europe in low season, the beaches before the winter crowds, the big US cities crisp and quiet. The first three weeks are the value; the fourth is the peak.

Nonstop from Chicago: Orlando (2h 30m), Nashville (1h 34m), New Orleans (2h 15m), Boston (2h 18m), San Juan (4h 44m), Miami (3h 10m), Phoenix (3h 55m), Washington (American, United, Southwest · 1h 45m), Los Angeles (4h 29m) and Cancun (3h 45m), and 6 more. One stop via Dallas: Las Vegas; via Toronto: San Jose Cabo; via Atlanta: Punta Cana. No recent searches for Honolulu, Puerto Vallarta, San Francisco, Denver and Austin.

Axel's pick: Orlando, nonstop and the lowest fare saved for these dates, from $171.

Where to fly from Chicago in November: the cheapest saved round trips within November 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 Nov.

Cheapest right now: Orlando from $171 · Nashville $197 · New Orleans from $232

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Flights from Chicago

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Cheapest places in November from other cities

Fares observed October 22 – 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
Orlando (MCO)Orlando's theme parksNonstop · 2h 30mfrom $171 (airline $180)Nov 7–14, 2026Check prices
Nashville (BNA)Nashville's honky-tonks and hot chickenNonstop · 1h 34m$197 (airline $208)Nov 14–21, 2026Check prices
New Orleans (MSY)New Orleans' French Quarter, food and musicNonstop · 2h 15mfrom $232 (airline $245)Nov 7–14, 2026Check prices
Las Vegas (LAS)Las Vegas' Strip, shows and day trips to the canyons1 stop via Dallas$237 (airline $250)Nov 10–17, 2026Check prices
Boston (BOS)Boston's Freedom Trail, universities and seafoodNonstop · 2h 18m$277 (airline $292)Nov 16–19, 2026Check prices
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNonstop · 4h 44m$286 (airline $302)Nov 10–17, 2026Check prices
Miami (MIA)Miami's South Beach, Little Havana and art decoNonstop · 3h 10m$289 (airline $306)Nov 19–23, 2026Check prices
Phoenix (PHX)Phoenix and Scottsdale's resorts, golf and desert hikingNonstop · 3h 55m$304 (airline $320)Nov 7–14, 2026Check prices
Washington (DCA)Washington's monuments and free museums, minutes from the airportNonstop · American, United, Southwest · 1h 45mfrom $326 (airline $344)Nov 5–12, 2026Check prices
Los Angeles (LAX)Los Angeles' beaches, Hollywood and museumsNonstop · 4h 29mfrom $373 (airline $394)Nov 12–19, 2026Check prices
Cancun (CUN)Cancún's hotel zone, the Riviera Maya and Mayan ruins nearbyNonstop · 3h 45mfrom $410 (airline $433)Nov 7–14, 2026Check prices
San Diego (SAN)San Diego's beaches, zoo and Balboa ParkNonstop · 4h 30m$432 (airline $456)Nov 24–29, 2026Check prices
New York (JFK)New York's museums, Broadway and neighborhoodsNonstop · American, Delta · 2h 28mfrom $557 (airline $588)Nov 21–28, 2026Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNonstop · United, Americanfrom $878 (airline $924)Nov 7–14, 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
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resorts1 stop via Atlanta$1,162 (airline $1,226)Nov 20–23, 2026Check prices
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNonstop · United, American, Southwest · 4h 08m$2,580 (airline $2,719) · 4 adultsNov 20–24, 2026Check prices
Oahu / Honolulu (HNL)Waikiki, Diamond Head and Pearl Harbor on OahuNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Puerto Vallarta (PVR)Puerto Vallarta's old town, beaches and Banderas BayNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNonstop · United, AmericanNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
San Francisco (SFO)San Francisco's Golden Gate, cable cars and wine country nearbyNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Denver (DEN)Denver's breweries and the Rockies within an hourNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Seattle (SEA)Seattle's Pike Place Market, waterfront and the mountainsNonstop · Alaska, Delta, UnitedNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Austin (AUS)Austin's live music, barbecue and swimming holesNo matching fare savedNov 7 – Nov 14, 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.

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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 November. Where to fly from Chicago in November: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more. The cheapest saved fares for trips within November, 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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