Cheap Flights from Boston, MA to Chicago, IL from $45
Return flight: Chicago – Boston
On Cheapflightsplus.com you will find 22 direct and 372 connecting flights from Boston to Chicago. You can compare airfare deals from 7 airlines and multiple travel sites from $45, 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: $45 (one-way), $77 (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 $45. The fastest direct flight takes 2h 47m and the fastest connecting – 4h 23m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $78 | 15:18 Boston Logan | 17:05 Chicago O'Hare International | 2h 47m | United Airlines | UA1989 |
| from $78 | 20:44 Boston Logan | 22:32 Chicago O'Hare International | 2h 48m | United Airlines | UA2229 |
| from $96 | 10:40 Boston Logan | 12:31 Chicago O'Hare International | 2h 51m | United Airlines | UA1298 |
| from $123 | 15:18 Boston Logan | 17:05 Chicago O'Hare International | 2h 47m | United Airlines | UA1032 |
| from $45 | 06:10 Boston Logan | 14:34 Chicago O'Hare International | 9h 24m layover 2h 45m - Miami | Spirit Airlines | NK296 NK866 |
| from $45 | 11:56 Boston Logan | 20:40 Chicago O'Hare International | 9h 44m layover 3h 3m - Miami | Spirit Airlines | NK2887 NK3 |
| from $54 | 17:42 Boston Logan | 23:29 Chicago O'Hare International | 6h 47m layover 0h 32m - Orlando | Spirit Airlines | NK2093 NK2190 |
| from $66 | 10:21 Boston Logan | 17:10 Chicago O'Hare International | 7h 49m layover 1h 25m - Dallas | Spirit Airlines | NK1837 NK1634 |
| from $66 | 07:00 Boston Logan | 18:43 Chicago O'Hare International | 12h 43m layover 6h 17m - Orlando | Spirit Airlines | NK643 NK506 |
| from $66 | 07:00 Boston Logan | 19:58 Chicago O'Hare International | 13h 58m layover 7h 30m - Orlando | Spirit Airlines | NK643 NK1109 |
| from $69 | 11:31 Boston Logan | 07:13+1 день Chicago Midway | 20h 42m layover 15h 49m - Savannah | Allegiant Air | G41152 G41163 |
| from $72 | 06:00 Boston Logan | 20:48 Chicago O'Hare International | 15h 48m layover 11h 55m - Baltimore | Spirit Airlines | NK1588 NK1187 |
| from $73 | 06:00 Boston Logan | 22:29 Chicago O'Hare International | 17h 29m layover 11h 5m - Tampa | Frontier Airlines | F91215 F92317 |
| from $75 | 06:00 Boston Logan | 09:23 Chicago O'Hare International | 4h 23m layover 0h 30m - Baltimore | Spirit Airlines | NK2106 NK2439 |
| from $76 | 10:51 Boston Logan | 20:17 Chicago Midway | 10h 26m layover 4h 19m - Orlando | Frontier Airlines | F91977 F93853 |
| from $76 | 10:51 Boston Logan | 00:10+1 день Chicago O'Hare International | 14h 19m layover 7h 54m - Orlando | Frontier Airlines | F91977 F92791 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 31, 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 |
|---|---|---|---|---|
|
06:10 — 08:05
|
06:10 — 08:05
UA1414
United Airlines
Boston — Chicago
|
2h 55m |
Find flight
from$78 |
|
|
07:44 — 09:39
|
07:44 — 09:39
UA1909
United Airlines
Boston — Chicago
|
2h 55m |
Find flight
from$78 |
|
|
07:44 — 09:39
|
07:44 — 09:39
UA1857
United Airlines
Boston — Chicago
|
2h 55m |
Find flight
from$78 |
|
|
07:45 — 09:41
|
07:45 — 09:41
UA2251
United Airlines
Boston — Chicago
|
2h 56m |
Find flight
from$78 |
|
|
07:45 — 09:41
|
07:45 — 09:41
UA449
United Airlines
Boston — Chicago
|
2h 56m |
Find flight
from$81 |
|
|
07:45 — 09:41
|
07:45 — 09:41
UA2401
United Airlines
Boston — Chicago
|
2h 56m |
Find flight
from$83 |
|
|
09:03 — 10:54
|
09:03 — 10:54
UA546
United Airlines
Boston — Chicago
|
2h 51m |
Find flight
from$78 |
|
|
09:03 — 10:54
|
09:03 — 10:54
UA600
United Airlines
Boston — Chicago
|
2h 51m |
Find flight
from$102 |
|
|
09:43 — 11:33
|
09:43 — 11:33
UA378
United Airlines
Boston — Chicago
|
2h 50m |
Find flight
from$78 |
|
|
09:43 — 11:33
|
09:43 — 11:33
UA365
United Airlines
Boston — Chicago
|
2h 50m |
Find flight
from$78 |
|
|
10:40 — 12:31
|
10:40 — 12:31
UA1298
United Airlines
Boston — Chicago
|
2h 51m |
Find flight
from$96 |
|
|
10:40 — 12:31
|
10:40 — 12:31
UA2430
United Airlines
Boston — Chicago
|
2h 51m |
Find flight
from$102 |
|
|
11:02 — 12:52
|
11:02 — 12:52
UA1314
United Airlines
Boston — Chicago
|
2h 50m |
Find flight
from$81 |
|
|
11:02 — 12:53
|
11:02 — 12:53
UA345
United Airlines
Boston — Chicago
|
2h 51m |
Find flight
from$84 |
|
|
12:45 — 14:35
|
12:45 — 14:35
UA1732
United Airlines
Boston — Chicago
|
2h 50m |
Find flight
from$78 |
|
|
15:15 — 17:05
|
15:15 — 17:05
UA1301
United Airlines
Boston — Chicago
|
2h 50m |
Find flight
from$81 |
|
|
15:16 — 17:05
|
15:16 — 17:05
UA1504
United Airlines
Boston — Chicago
|
2h 49m |
Find flight
from$84 |
|
|
15:18 — 17:05
|
15:18 — 17:05
UA1989
United Airlines
Boston — Chicago
|
2h 47m |
Find flight
from$78 |
|
|
15:18 — 17:05
|
15:18 — 17:05
UA1032
United Airlines
Boston — Chicago
|
2h 47m |
Find flight
from$123 |
|
|
16:27 — 18:20
|
16:27 — 18:20
UA2040
United Airlines
Boston — Chicago
|
2h 53m |
Find flight
from$101 |
|
|
18:11 — 20:05
|
18:11 — 20:05
UA1015
United Airlines
Boston — Chicago
|
2h 54m |
Find flight
from$78 |
|
|
20:44 — 22:32
|
20:44 — 22:32
UA2229
United Airlines
Boston — Chicago
|
2h 48m |
Find flight
from$78 |
|
|
05:45 — 17:44
|
05:45 — 08:52
NK2257
Spirit Airlines
Boston — Orlando
6h 27m stop
21:25 — 23:29
NK2190
Spirit Airlines
Orlando — Chicago
|
12h 59m including layover |
Find flight
from$79 |
|
|
06:10 — 14:34
|
06:10 — 09:32
NK296
Spirit Airlines
Boston — Miami
2h 45m stop
12:17 — 14:34
NK866
Spirit Airlines
Miami — Chicago
|
9h 24m including layover |
Find flight
from$45 |
|
|
06:10 — 17:37
|
06:10 — 09:32
NK296
Spirit Airlines
Boston — Miami
5h 48m stop
15:20 — 17:37
NK1026
Spirit Airlines
Miami — Chicago
|
12h 27m including layover |
Find flight
from$45 |
|
|
07:00 — 18:43
|
07:00 — 10:16
NK643
Spirit Airlines
Boston — Orlando
6h 17m stop
16:33 — 18:43
NK506
Spirit Airlines
Orlando — Chicago
|
12h 43m including layover |
Find flight
from$66 |
|
|
07:00 — 19:58
|
07:00 — 10:16
NK643
Spirit Airlines
Boston — Orlando
7h 30m stop
17:46 — 19:58
NK1109
Spirit Airlines
Orlando — Chicago
|
13h 58m including layover |
Find flight
from$66 |
|
|
08:08 — 12:39
|
08:08 — 10:17
NK2517
Spirit Airlines
Boston — Myrtle Beach
56m stop
11:36 — 12:46
NK2520
Spirit Airlines
Myrtle Beach — Chicago
|
5h 31m including layover |
Find flight
from$81 |
|
|
08:47 — 16:40
|
08:47 — 10:58
F93057
Frontier Airlines
Boston — Raleigh
4h 13m stop
15:38 — 17:08
F93351
Frontier Airlines
Raleigh — Chicago
|
8h 53m including layover |
Find flight
from$81 |
|
|
10:21 — 17:10
|
10:21 — 13:31
NK1837
Spirit Airlines
Boston — Dallas
1h 25m stop
14:56 — 17:10
NK1634
Spirit Airlines
Dallas — Chicago
|
7h 49m including layover |
Find flight
from$66 |
|
|
10:51 — 20:17
|
09:40 — 12:55
F91977
Frontier Airlines
Boston — Orlando
4h 19m stop
18:20 — 20:17
F93853
Frontier Airlines
Orlando — Chicago
|
10h 26m including layover |
Find flight
from$76 |
|
|
11:31 — 07:13
+1 day
|
11:31 — 14:11
G41152
Allegiant Air
Boston — Savannah
15h 49m stop
06:00 — 07:15
G41163
Allegiant Air
Savannah — Chicago
|
20h 42m including layover |
Find flight
from$69 |
|
|
11:56 — 20:40
|
11:56 — 15:17
NK2887
Spirit Airlines
Boston — Miami
3h 3m stop
18:20 — 20:40
NK3
Spirit Airlines
Miami — Chicago
|
9h 44m including layover |
Find flight
from$45 |
|
|
12:37 — 14:03
+1 day
|
12:37 — 14:56
G43061
Allegiant Air
Boston — Knoxville
22h 33m stop
13:29 — 14:03
G43062
Allegiant Air
Knoxville — Chicago
|
26h 26m including layover |
Find flight
from$84 |
|
|
17:42 — 23:29
|
17:42 — 20:53
NK2093
Spirit Airlines
Boston — Orlando
32m stop
21:25 — 23:29
NK2190
Spirit Airlines
Orlando — Chicago
|
6h 47m including layover |
Find flight
from$54 |
|
|
17:42 — 20:03
+1 day
|
17:42 — 20:53
NK2093
Spirit Airlines
Boston — Orlando
21h 2m stop
17:55 — 20:03
NK2541
Spirit Airlines
Orlando — Chicago
|
27h 21m including layover |
Find flight
from$78 |
|
|
18:59 — 23:37
|
18:59 — 20:25
UA1308
United Airlines
Boston — Newark
1h 30m stop
21:55 — 23:37
UA1308
United Airlines
Newark — Chicago
|
5h 38m including layover |
Find flight
from$88 |
|
|
20:39 — 08:55
+1 day
|
20:39 — 00:15
NK1231
Spirit Airlines
Boston — Miami
6h 25m stop
06:40 — 08:55
NK1986
Spirit Airlines
Miami — Chicago
|
13h 16m including layover |
Find flight
from$81 |
|
|
19:47 — 23:29
+1 day
|
19:47 — 21:21
NK2523
Spirit Airlines
Boston — Baltimore
15h 30m stop
12:51 — 15:14
NK1961
Spirit Airlines
Baltimore — Orlando
6h 11m stop
21:25 — 23:29
NK2190
Spirit Airlines
Orlando — Chicago
|
28h 42m including layover |
Find flight
from$90 |
|
*Departure and arrival times - local. Updated on May 31, 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 21:40 from 4 Boston airports and arrive 05:30 to 21:40 to 7 Chicago airports. Average flight time is 2h 51m.
- The fastest flight 2h 47m
- Average flight time 2h 51m
- The earliest flight 05:30
- The latest flight 21:40
- Distance 852 ml
The cheapest months to travel to Chicago are august (from 61 $), october (from 70 $), may (from 72 $).
The most expensive months are january (from 294 $), december (from 122 $), september (from 93 $).
What is the lowest airfare Boston to Chicago?
The cheapest plane ticket found by our users is $45. This airfare is for economy class on one-way NK2887 flight by Spirit Airlines for August 27, 2025 which leaves Logan in Boston at 11:56 am and arrives at Chicago O'Hare International at 20:40.
Economy class
$45
Business class
?
First class
?
Popular Airlines on the Route
The flight Boston — Chicago is served by 7 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by United Airlines - 174 departures per week at the price of from $ 78 . And the most expensive tickets are offered by United Airlines airline - from $ 518.
Direct flights
There are 22 nonstop flights on the route. The fastest direct flight is UA1989 by United Airlines takes 2h 47m and the cheapest is NK2887 by Spirit Airlines for $78.
- from $78Find
See more direct flights
Connecting Flights
There are 372 flights with layovers on the route. The fastest connecting flight is NK2106 by Spirit Airlines takes 4h 23m and the cheapest is NK2887 by Spirit Airlines for $45.
- from $88Find
- AS - Alaska Airlinesfrom $157Find
- F9 - Frontier Airlinesfrom $73Find
- SY - Sun Country Airlinesfrom $108Find
- HA - Hawaiian Airlinesfrom $177Find
- NK - Spirit Airlinesfrom $45Find
- G4 - Allegiant Airfrom $69Find
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 $45Find
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 7 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.
- from $57Find
- from $67Find
- from $59Find
- from $56Find
- from $64Find
- from $65Find
- from $71Find
- from $63Find
- from $63Find
- from $60Find
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.
- from $76Find
- from $76Find
- from $54Find
- from $54Find
- from $69Find
- from $77Find
- from $78Find
- from $66Find
- from $77Find
- from $67Find
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.