Boston to Chicago flights (BOS → ORD)
Looking for Boston to Chicago flights? Cheapest round-trip I’ve found: US$215 on American, non-stop, departing 2026-10-15. That’s US$80 below the typical price for this route. Cheap flights from Boston to Chicago change daily — I re-check this route three times a day.
Deal score: Good price — cheaper than 60% of prices I’ve seen on this route.
Non-stopstops
3h 7mflight time
Oct 2026cheapest departure window
US$295typical price
Best months to fly Boston to Chicago
| Month | Cheapest seen |
|---|---|
| October | US$189 |
| December | US$189 |
| September | US$249 |
| February | US$256 |
How to book this fare
I don’t sell tickets — I track prices and point you to where to look. To book Boston to Chicago flights:
- Search Boston to Chicago on Google Flights for the dates shown above (Oct 2026) — the fare I found is usually still available there.
- Compare the same dates on metasearch sites like Skyscanner or KAYAK to confirm you’re seeing the lowest price.
- Book directly with the airline when you can — it’s often the same price and makes changes or cancellations much easier.
Fares change constantly. If the price has moved, check back — I re-check this route daily.
Other Boston to … flights
- Boston to Tokyo Narita flights — US$1,059
- Boston to Bali flights — US$1,020
- Boston to Santiago flights — US$545
- Boston to Edmonton flights — US$325
- Boston to Dublin flights — US$434
- Boston to Budapest flights — US$683
- Boston to Montreal flights — US$325
- Boston to Zagreb flights — US$775
All flights to Chicago · All flights from Boston
Prices last checked: 2026-09-24, 2:15:30 p.m.. Prices are indicative and change quickly — confirm on the airline site before booking. See how I find these deals.