Chicago to Boston

1 ways to travelfastest 2h 20mfly from €104
Photo: jacob Licht / Unsplash

How the cheapest fare moved

Nov 12: €104 €104 Nov 7 Nov 12 low €104 · high €138

Departure-day prices · September 2023 Chicago → Boston

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Return-day prices · September 2023 Boston → Chicago

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Best time to visit Boston — climate

Jan: ~0°C daytime, 7 rainy days 0° JanFeb: ~2°C daytime, 9 rainy days 2° FebMar: ~10°C daytime, 8 rainy days 10° MarApr: ~15°C daytime, 13 rainy days 15° AprMay: ~19°C daytime, 13 rainy days 19° MayJun: ~25°C daytime, 9 rainy days 25° JunJul: ~29°C daytime, 13 rainy days 29° JulAug: ~27°C daytime, 6 rainy days 27° AugSep: ~23°C daytime, 9 rainy days 23° SepOct: ~17°C daytime, 8 rainy days 17° OctNov: ~10°C daytime, 12 rainy days 10° NovDec: ~2°C daytime, 9 rainy days 2° Dec

Best value: Sep — fares from €155 and ~23°C daytime.

Flights from Chicago to Boston start around €104 (typically 1 stop). Range seen recently: €104–194, based on 12 fares found by travellers.

Fly (from €104)
2h 20mduration
€104–194recent fares
Book
Cheapest cached fares Chicago → Boston; typically 1 stop (e.g. F9). · Based on 12 fares found by travellers in the last 48h

Cheapest round trips to Boston

Fares found by travellers in the last 48 hours — refreshed daily.

Nov 21 – Nov 22 Southwest Airlines · Direct · 2h 20m €249 Book
Nov 22 – Nov 27 Frontier Airlines · 1 stop · 6h 10m €253 Book
Jan 1 – Jan 4 jetBlue · Direct · 2h 26m €257 Book
Nov 13 – Nov 15 United Airlines · Direct · 2h 19m €261 Book
Nov 26 – Nov 30 Frontier Airlines · 1 stop · 6h 10m €277 Book
Nov 14 – Nov 15 jetBlue · Direct · 2h 49m €341 Book
Nov 25 – Nov 29 Southwest Airlines · Direct · 2h 15m €444 Book
Nov 24 – Nov 29 Frontier Airlines · 1 stop · 5h 53m €477 Book

Weather in Boston

Thu 🌦️ 12° 6° 💧75%
Fri 🌦️ 8° 3° 💧81%
Sat ☁️ 8° 2° 💧11%
Sun ☁️ 9° 3° 💧0%
Mon ☀️ 10° 3° 💧0%
Tue ☀️ 11° 3° 💧0%
Wed ☀️ 14° 5° 💧0%

In Sep, Boston typically sees ~22°C daytime highs and 7 rainy days.

Where to stay in Boston

3★+ hotels from €113/night (39 hotels sampled, ~3 weeks out).

The Revolution Hotel hotel · Boston
from €113/night★ 3
Hampton by Hilton at the Boston Seaport District hotel · Boston
from €115/night★ 3
Hilton Boston Park Plaza hotel · Boston
from €120/night★ 4

Good to know

Time difference+1h
Time in the air2h 15m

Things to do in Boston

Top-rated tours and tickets from €36 — book ahead for the popular ones.

Tours and tickets provided by Viator (a Tripadvisor company). Some links earn Stayonomy a commission.

About Boston

A city of history and tradition, Boston offers a proud legacy of culture, education, and numerous sporting championships. The "shining city on a hill"s independent spirit has been displayed to the world ever since colonists were angry over a British tax on their beloved tea and dumped shiploads of it into the harbor in protest. In the early 1600s, the peninsula in Massachusetts that would become known as Boston was controlled by Native Americans until John Smith (English soldier, explorer, colonial governor, Admiral of New England, and author) …

Read the full Boston guide

Guide content from Wikivoyage contributors (CC BY-SA).

Round out the trip

Popular from Chicago

Cheapest destinations travellers searched recently — refreshed daily.

Flight prices are real fares travellers found in the last 48 hours, refreshed daily — the booking site confirms the final price. Train, bus and ferry fares are shown on the operators' booking sites. Weather data by Open-Meteo; exchange rates: ECB reference. Data updated 2026-11-12. Some links earn Stayonomy a commission at no cost to you.