Boston to Chicago: what the flight costs
In the last 60 days we checked this route 11 times. The typical return was £291 per person and the lowest £225, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £225 |
| Typical (median) | £291 |
| Price checks, 60 days | 11 |
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Trips we picked on this route
Just found · from BostonWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Hyatt Place in The Loop: 8.2 from 1,959 reviews, free cancellation
- Fare of $386 per person matches the median of earlier checks
- Saturday high of 58°F with a 7% rain chance, Sunday 0%
£1,226 for two · 2 nights · flights, hotel, taxes & fees
Flights £582 + hotel £644, taxes in · a checked bag each adds about £181
Frontier · with a stop · 6h 34m
The catch: Frontier's fare has one stop and takes 6h 34m, Friday has a 78% drizzle chance, and a checked bag is about $240 for two.
Worth it if you want a walkable city weekend of museums and food; skip it if a 6h 34m trip with a stop would eat your Friday.
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| 15 Oct 2026 | 30 Oct – 1 Nov 2026 | £269 | B6 | nonstop | 3h 14m | Kiwi.com |
| 15 Oct 2026 | 23 – 25 Oct 2026 | £300 | B6 + F9 | with a stop | 2h 52m | Kiwi.com |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £291 | Frontier | with a stop | 6h 34m | Google Flights |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £292 | B6 + F9 | with a stop | 3h 2m | Kiwi.com |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £317 | B6 + F9 | with a stop | 2h 52m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £291 | B6 | with a stop | 17h 56m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £240 | Frontier | with a stop | 6h 34m | Google Flights |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £225 | Frontier | with a stop | 6h 34m | Google Flights |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £290 | B6 + F9 | with a stop | 2h 52m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £317 | B6 + F9 | with a stop | 3h 2m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £403 | UA | nonstop | 2h 52m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about Boston to Chicago
What does a return from Boston to Chicago usually cost?
Over the last 60 days the typical price we found was £291 per person, taxes and fees included, across 11 checks; the lowest was £225.
When is the best time to fly from Boston to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from Boston to Chicago?
No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
Prices converted from US dollars at the rate of 15 Oct 2026.