Cheap Flights from Boston, MA to Chicago, IL from $98
Return flight: Chicago – Boston
On Cheapflightsplus.com you will find 3 direct and 50 connecting flights from Boston to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $98, book and save on cheap plane tickets and last minute offers. Also check out BOS-CHI flight schedule to find best flight time, convenient departure and arrival airports.
Find One-Way and Round-Trip Boston to Chicago Flight Deals
To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights».
To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight.
Cheapest flights in November: $98 (one-way), $168 (round-trip).
Direct flights
Check prices for return flight
Best Flights from Boston to Chicago Today
Take a look at the list of non stop flights and flights with layovers from Boston to Chicago with the lowest price of $98. The fastest direct flight takes 2h 50m and the fastest connecting – 4h 45m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $107 | 09:43 Boston Logan | 11:33 Chicago O'Hare International | 2h 50m | United Airlines | UA365 |
| from $107 | 12:30 Boston Logan | 14:20 Chicago O'Hare International | 2h 50m | United Airlines | UA1732 |
| from $107 | 07:45 Boston Logan | 09:41 Chicago O'Hare International | 2h 56m | United Airlines | UA2251 |
| from $98 | 14:53 Boston Logan | 22:22 Chicago O'Hare International | 8h 29m layover 2h 12m - Orlando | Spirit Airlines | NK2179 NK2343 |
| from $111 | 16:12 Boston Logan | 15:43+1 день Chicago O'Hare International | 24h 31m layover 19h 49m - Myrtle Beach | Spirit Airlines | NK2512 NK2074 |
| from $111 | 12:25 Boston Logan | 15:43+1 день Chicago O'Hare International | 28h 18m layover 23h 44m - Myrtle Beach | Spirit Airlines | NK2301 NK2074 |
| from $133 | 06:05 Boston Logan | 23:59 Chicago O'Hare International | 18h 54m layover 12h 14m - Miami | Spirit Airlines | NK2448 NK2 |
| from $133 | 16:38 Boston Logan | 16:10+1 день Chicago O'Hare International | 24h 32m layover 18h 10m - Orlando | Spirit Airlines | NK2723 NK2410 |
| from $141 | 13:00 Boston Logan | 17:10 Chicago O'Hare International | 5h 10m layover 1h 12m - Washington D.C. | United Airlines | UA2692 UA265 |
| from $142 | 14:40 Boston Logan | 18:25 Chicago O'Hare International | 4h 45m layover 0h 47m - Washington D.C. | United Airlines | UA721 UA2497 |
| from $142 | 19:12 Boston Logan | 23:15 Chicago O'Hare International | 5h 3m layover 1h 15m - Washington D.C. | United Airlines | UA2136 UA1738 |
| from $142 | 05:30 Boston Logan | 09:36 Chicago O'Hare International | 5h 6m layover 1h 10m - Washington D.C. | United Airlines | UA1734 UA2401 |
| from $142 | 14:40 Boston Logan | 19:48 Chicago O'Hare International | 6h 8m layover 2h 17m - Washington D.C. | United Airlines | UA721 UA2304 |
| from $144 | 18:55 Boston Logan | 19:07+1 день Chicago O'Hare International | 25h 12m layover 18h 31m - Miami | Spirit Airlines | NK2303 NK2125 |
| from $141 | 10:34 Boston Logan | 11:10+1 день Chicago O'Hare International | 25h 36m layover 4h 53m - Orlando 13h 2m - Baltimore | Spirit Airlines | NK426 NK2022 NK2072 |
| from $164 | 15:25 Boston Logan | 11:10+1 день Chicago O'Hare International | 20h 45m layover 2h 23m - Miami 10h 5m - Baltimore | Spirit Airlines | NK2839 NK2737 NK2072 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 24, 2025
Flight Schedule Boston (Massachusetts) to Chicago (Illinois)
Full flight schedule will help you in detecting at what time planes fly from Boston to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
| Departure | Arrival | Flight Details | Flight Duration | Price |
|---|---|---|---|---|
|
07:45 — 09:41
|
07:45 — 09:41
UA2251
United Airlines
Boston — Chicago
|
2h 56m |
Find flight
from$107 |
|
|
09:43 — 11:33
|
09:43 — 11:33
UA365
United Airlines
Boston — Chicago
|
2h 50m |
Find flight
from$107 |
|
|
12:30 — 14:20
|
12:30 — 14:20
UA1732
United Airlines
Boston — Chicago
|
2h 50m |
Find flight
from$107 |
|
|
05:30 — 09:36
|
05:30 — 07:10
UA1734
United Airlines
Boston — Washington D.C.
1h 10m stop
08:20 — 09:36
UA2401
United Airlines
Washington D.C. — Chicago
|
5h 6m including layover |
Find flight
from$142 |
|
|
05:30 — 17:10
|
05:30 — 07:10
UA1734
United Airlines
Boston — Washington D.C.
8h 45m stop
15:55 — 17:10
UA265
United Airlines
Washington D.C. — Chicago
|
12h 40m including layover |
Find flight
from$247 |
|
|
06:05 — 19:07
|
06:05 — 09:33
NK2448
Spirit Airlines
Boston — Miami
7h 16m stop
16:49 — 19:07
NK2125
Spirit Airlines
Miami — Chicago
|
14h 2m including layover |
Find flight
from$98 |
|
|
06:05 — 23:59
|
06:05 — 09:33
NK2448
Spirit Airlines
Boston — Miami
12h 14m stop
21:47 — 23:59
NK2
Spirit Airlines
Miami — Chicago
|
18h 54m including layover |
Find flight
from$133 |
|
|
07:10 — 17:00
|
07:10 — 08:35
UA570
United Airlines
Boston — Newark
6h 50m stop
15:25 — 17:00
UA2394
United Airlines
Newark — Chicago
|
10h 50m including layover |
Find flight
from$260 |
|
|
08:05 — 18:29
|
08:05 — 09:30
UA309
United Airlines
Boston — Newark
7h 19m stop
16:49 — 18:29
UA661
United Airlines
Newark — Chicago
|
11h 24m including layover |
Find flight
from$260 |
|
|
09:30 — 14:29
|
09:30 — 11:13
UA2098
United Airlines
Boston — Washington D.C.
2h 2m stop
13:15 — 14:29
UA2331
United Airlines
Washington D.C. — Chicago
|
5h 59m including layover |
Find flight
from$149 |
|
|
10:34 — 22:22
|
10:34 — 13:47
NK426
Spirit Airlines
Boston — Orlando
6h 36m stop
20:23 — 22:22
NK2343
Spirit Airlines
Orlando — Chicago
|
12h 48m including layover |
Find flight
from$98 |
|
|
12:25 — 15:43
+1 day
|
12:25 — 14:34
NK2301
Spirit Airlines
Boston — Myrtle Beach
23h 44m stop
14:18 — 15:43
NK2074
Spirit Airlines
Myrtle Beach — Chicago
|
28h 18m including layover |
Find flight
from$111 |
|
|
13:00 — 17:10
|
13:00 — 14:43
UA2692
United Airlines
Boston — Washington D.C.
1h 12m stop
15:55 — 17:10
UA265
United Airlines
Washington D.C. — Chicago
|
5h 10m including layover |
Find flight
from$141 |
|
|
13:00 — 19:48
|
13:00 — 14:43
UA2692
United Airlines
Boston — Washington D.C.
3h 57m stop
18:40 — 19:48
UA2304
United Airlines
Washington D.C. — Chicago
|
7h 48m including layover |
Find flight
from$141 |
|
|
14:53 — 22:22
|
14:53 — 18:11
NK2179
Spirit Airlines
Boston — Orlando
2h 12m stop
20:23 — 22:22
NK2343
Spirit Airlines
Orlando — Chicago
|
8h 29m including layover |
Find flight
from$98 |
|
|
14:53 — 16:10
+1 day
|
14:53 — 18:11
NK2179
Spirit Airlines
Boston — Orlando
19h 56m stop
14:07 — 16:10
NK2410
Spirit Airlines
Orlando — Chicago
|
26h 17m including layover |
Find flight
from$133 |
|
|
15:25 — 09:22
+1 day
|
15:25 — 19:06
NK2839
Spirit Airlines
Boston — Miami
11h 54m stop
07:00 — 09:22
NK2530
Spirit Airlines
Miami — Chicago
|
18h 57m including layover |
Find flight
from$133 |
|
|
16:12 — 15:43
+1 day
|
16:12 — 18:29
NK2512
Spirit Airlines
Boston — Myrtle Beach
19h 49m stop
14:18 — 15:43
NK2074
Spirit Airlines
Myrtle Beach — Chicago
|
24h 31m including layover |
Find flight
from$111 |
|
|
16:38 — 16:10
+1 day
|
16:38 — 19:57
NK2723
Spirit Airlines
Boston — Orlando
18h 10m stop
14:07 — 16:10
NK2410
Spirit Airlines
Orlando — Chicago
|
24h 32m including layover |
Find flight
from$133 |
|
|
18:55 — 19:07
+1 day
|
18:55 — 22:18
NK2303
Spirit Airlines
Boston — Miami
18h 31m stop
16:49 — 19:07
NK2125
Spirit Airlines
Miami — Chicago
|
25h 12m including layover |
Find flight
from$144 |
|
|
18:55 — 23:59
+1 day
|
18:55 — 22:18
NK2303
Spirit Airlines
Boston — Miami
23h 29m stop
21:47 — 23:59
NK2
Spirit Airlines
Miami — Chicago
|
30h 4m including layover |
Find flight
from$144 |
|
|
19:05 — 23:25
|
19:05 — 20:45
UA3571
United Airlines
Boston — Newark
59m stop
21:44 — 23:25
UA1308
United Airlines
Newark — Chicago
|
5h 20m including layover |
Find flight
from$214 |
|
|
19:12 — 23:15
|
19:00 — 20:46
UA2136
United Airlines
Boston — Washington D.C.
1h 15m stop
22:18 — 23:30
UA1738
United Airlines
Washington D.C. — Chicago
|
5h 3m including layover |
Find flight
from$142 |
|
|
20:23 — 13:01
+1 day
|
20:23 — 23:52
AS249
Alaska Airlines
Boston — San Francisco
6h 38m stop
06:30 — 13:01
UA587
United Airlines
San Francisco — Chicago
|
17h 38m including layover |
Find flight
from$727 |
|
|
10:34 — 11:10
+1 day
|
10:34 — 13:47
NK426
Spirit Airlines
Boston — Orlando
4h 53m stop
18:40 — 21:02
NK2022
Spirit Airlines
Orlando — Baltimore
13h 2m stop
10:04 — 11:10
NK2072
Spirit Airlines
Baltimore — Chicago
|
25h 36m including layover |
Find flight
from$141 |
|
|
15:25 — 11:10
+1 day
|
15:25 — 19:06
NK2839
Spirit Airlines
Boston — Miami
2h 23m stop
21:29 — 23:59
NK2737
Spirit Airlines
Miami — Baltimore
10h 5m stop
10:04 — 11:10
NK2072
Spirit Airlines
Baltimore — Chicago
|
20h 45m including layover |
Find flight
from$164 |
|
*Departure and arrival times - local. Updated on July 24, 2025
Flight Information
Below we will explain in detail what the flights cost on the destination from Boston to Chicago depends on and how to choose the most interesting flight option for you.
Distance between Boston and Chicago is 1370 miles. Time difference between the cities is 1h. Airplanes depart 05:30 to 20:23 from 4 Boston airports and arrive 05:30 to 20:23 to 7 Chicago airports. Average flight time is 2h 50m.
- The fastest flight 2h 50m
- Average flight time 2h 50m
- The earliest flight 05:30
- The latest flight 20:23
- Distance 852 ml
The cheapest months to travel to Chicago are august (from 98 $), october (from 110 $), september (from 113 $).
The most expensive months are november (from 143 $), june (from 138 $), may (from 138 $).
What is the lowest airfare Boston to Chicago?
The cheapest plane ticket found by our users is $98. This airfare is for economy class on one-way NK2448 flight by Spirit Airlines for August 30, 2025 which leaves Logan in Boston at 06:05 am and arrives at Chicago O'Hare International at 19:07.
Economy class
$98
Business class
?
First class
?
Popular Airlines on the Route
The flight Boston — Chicago is served by 4 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by United Airlines - 21 departures per week at the price of from $ 107 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 727.
Direct flights
There are 3 nonstop flights on the route. The fastest direct flight is UA365 by United Airlines takes 2h 50m and the cheapest is NK2448 by Spirit Airlines for $107.
- from $107Find
See more direct flights
Connecting Flights
There are 50 flights with layovers on the route. The fastest connecting flight is UA721 by United Airlines takes 4h 45m and the cheapest is NK2448 by Spirit Airlines for $98.
- from $141Find
- AS - Alaska Airlinesfrom $727Find
- HA - Hawaiian Airlinesfrom $228Find
- NK - Spirit Airlinesfrom $98Find
See more connecting flights
Airports
You can fly from Boston to Chicago from 4 airports (Boston City Heliport, Boston RT128 Rail, Boston South Rail, Logan).
Boston airports
- Boston City Heliport-JBCFind
- Boston RT128 Rail-ZRUFind
- Boston South Rail-ZTOFind
- Logan-BOSfrom $98Find
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from Boston by 4 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top Domestic Destinations from Boston
You may also consider searching for discounted plane tickets to some other popular places from Boston within United States.
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Top International Destinations from Boston
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
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How to book a plane ticket yourself?
- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
- Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
- That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
To find a plane ticket, please select dates.