Round trip from
$125
15 Nov – 16 Nov · United Airlines · direct
found today
Direct flights from
$125
15 Nov – 16 Nov · United Airlines
Your search is opening in a new tab
Come back here when you have your fare. For this trip you may also want:
-
1366 km
Distance
-
2 h 45 min
Shortest flight
-
75%
Direct flights
-
5
Airlines
-
$134
One way from
-
$125
Round trip from
The route at a glance
About 1366 km separate Boston and Chicago; the quickest flight is 2 h 45 min and a typical one 3 h 2 min.
75% of the cheapest tickets are direct; Southwest Airlines carries 42% of them.
Most cheap flights leave from Logan International Airport (3 km from the centre of Boston).
Most land at O'Hare International Airport (25 km from the centre of Chicago).
A one-way ticket starts at $134, a round trip at $125.
Cheapest price by month
| Month | Round trip from |
|---|---|
| November 2026 | $125 |
| December 2026 | $286 |
| January 2027 | $326 |
| February 2027 | $210 |
| June 2027 | $331 |
| August 2027 | $244 |
Cheapest day to fly
Looking two months ahead, 20 November is the cheapest date to leave, at $134.
Saturday is the cheapest day of the week to fly.
| Mon | Tue | Wed | Thu | Fri | Sat | Sun |
|---|---|---|---|---|---|---|
| 4 $144 |
5 $149 |
6 $149 |
7 $149 |
8 $149 |
||
| 9 $155 |
10 $153 |
11 $153 |
12 $153 |
13 $151 |
14 $135 |
15 $135 |
| 16 $135 |
22 $150 |
23 $157 |
24 $164 |
25 $140 |
Cheaper More expensive
- $134 — Friday, Nov. 20, 2026
- $135 — Saturday, Nov. 14, 2026
- $135 — Sunday, Nov. 15, 2026
- $135 — Monday, Nov. 16, 2026
- $135 — Tuesday, Nov. 17, 2026
- $135 — Wednesday, Nov. 18, 2026
- $135 — Thursday, Nov. 19, 2026
- $140 — Friday, Dec. 25, 2026
- $144 — Wednesday, Nov. 4, 2026
- $149 — Thursday, Nov. 5, 2026
- $149 — Friday, Nov. 6, 2026
- $149 — Saturday, Nov. 7, 2026
- $149 — Sunday, Nov. 8, 2026
- $150 — Tuesday, Dec. 22, 2026
- $151 — Friday, Nov. 13, 2026
- $153 — Tuesday, Nov. 10, 2026
- $153 — Wednesday, Nov. 11, 2026
- $153 — Thursday, Nov. 12, 2026
- $155 — Monday, Nov. 9, 2026
- $157 — Wednesday, Dec. 23, 2026
- $164 — Thursday, Dec. 24, 2026
Price trend, last 30 days
Prices over the past month ranged from $125 to $204, with $174 the usual level.
Today's price is 28% below that average — a good moment to book.
- 5 October — $190
- 10 October — $190
- 15 October — $190
- 20 October — $204
- 25 October — $194
- 30 October — $125
- 4 November — $125
Trip length and timing
The cheapest tickets are for stays of about 3 nights (the very cheapest: 1 night), booked around 12 days ahead.
Airlines on this route
Airports used
Trip essentials
Car rental in Chicago
Pick up a car at the airport.
Mobile data in Chicago
An eSIM with local data, set up before you land.
by Airalo
Airport transfer in Chicago
A fixed-price ride from the airport, booked ahead.
by Kiwitaxi
Flight delayed or cancelled?
You may be owed up to €600 for a disrupted EU flight. Check in two minutes.
by AirHelp
Flight deals from Boston in Telegram
A daily digest of the cheapest fares from your city and instant alerts when a price drops. Free, no account needed.
Questions and answers
- What is the cheapest price for flights from Boston to Chicago?
- The cheapest round-trip ticket found recently costs $125.
- Which month is the cheapest to fly from Boston to Chicago?
- November 2026 is currently the cheapest month, with tickets from $125.
- Are there direct flights from Boston to Chicago?
- Yes. Direct flights were found from $125.
- Which airlines fly from Boston to Chicago?
- Airlines found on this route: American Airlines, jetBlue, Frontier Airlines, United Airlines, Southwest Airlines.
- How far is Chicago from Boston?
- The distance is about 1366 km. A direct flight takes about 3 h 4 min.
- How long is the flight from Boston to Chicago?
- The shortest flight takes 2 h 45 min; most take about 3 h 2 min.
- Which airports do flights from Boston to Chicago use?
- Most depart from Logan International Airport and arrive at O'Hare International Airport.
- What is the cheapest day of the week to fly from Boston to Chicago?
- In the next two months, Saturday departures are the cheapest; the single cheapest day is 20 November at $134.