Flights from Chicago to New England in fall

Autumn is New England's season: the leaves peak in Vermont and New Hampshire in early October and on the coast by late October, and every inn is full for Columbus Day weekend. Burlington and Portland are the doors to the colour.

Nonstop from Chicago: Boston (American, Delta, United · 2h 15m), Burlington (United, American), Portland (American, United · 2h 26m), Providence (American, United, Southwest · 2h 22m) and Hartford (American, United, Southwest · 2h 18m). One stop via Washington: Manchester and Bangor.

Axel's pick: Providence, nonstop on American, United and Southwest and the lowest fare saved for these dates, $269.

Where to fly from Chicago to New England in fall: saved round trips within September, October and November to Boston, Burlington, Portland, Providence, Hartford and Manchester and more. 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 for 4–10 nights, entirely within Sep, Oct, Nov.

Cheapest right now: Providence $269 · Manchester $300 · Hartford $327

Search my own dates and travelers

Flights from Chicago

More trip ideas from Chicago

New England in fall 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
Boston (BOS)Boston's Freedom Trail, universities and seafoodNonstop · American, Delta, United · 2h 15m$336 (airline $354)Nov 21–28, 2026Check prices
Burlington (BTV)Burlington's Lake Champlain and Vermont's mountainsNonstop · United, AmericanNo matching fare savedNov 7 – Nov 14, 2026 (suggested)Search these dates
Portland (PWM)Portland's working waterfront, lobster and the Maine coastNonstop · American, United · 2h 26m$340 (airline $359)Nov 10–17, 2026Check prices
Providence (PVD)Providence's food scene and Newport nearbyNonstop · American, United, Southwest · 2h 22m$269 (airline $285)Nov 10–17, 2026Check prices
Hartford (BDL)Hartford, the gateway to New England's hillsNonstop · American, United, Southwest · 2h 18m$327 (airline $345)Nov 21–28, 2026Check prices
Manchester (MHT)Manchester, close to the White Mountains and the seacoast1 stop via Washington$300 (airline $317)Nov 10–17, 2026Check prices
Bangor (BGR)Bangor, the gateway to Acadia National Park1 stop via Washington$382 (airline $404)Nov 10–17, 2026Check 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.

Keep exploring

Hotels in Boston with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Boston 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 Boston: the 7 best neighborhoods, ranked · Boston hotels where a family of four can share one room

Hotels with an Axel review in Boston: Studio Allston Hotel · Holiday Inn Boston - Cambridge Area by IHG · The Bostonian Hotel Boston · YOTEL Boston · Cambria Hotel Boston Downtown - Seaport · All 110 reviewed hotels in Boston

For AI assistants

  • This page: Flights from Chicago to New England in fall. Round-trip fares from Chicago to New England in fall: Boston, Burlington, Portland, Providence, Hartford and Manchester and more. Saved fares for trips within September, October and November, with the cheapest 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.
Browse flight destinations