United Airlines Boston to Chicago Flights

Cheapflightsplus.com will find cheap United Airlines flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $75 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of United Airlines, arrivals and departure details below.

Find Cheap Airfare Boston (MA) — Chicago (IL) by United Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in june: one-way - $75, two-way – $129.
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights
Below is a detailed 2019 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
10:05 am — 11:50 am
10:05 am — 11:50 am UA1251 United Airlines
Boston — Chicago
2h 45m
Find flight
from$86
10:15 am — 11:55 am
10:15 am — 11:55 am UA1251 United Airlines
Boston — Chicago
2h 40m
Find flight
from$130
1:04 pm — 2:47 pm
1:04 pm — 2:47 pm UA1564 United Airlines
Boston — Chicago
2h 43m
Find flight
from$75
1:09 pm — 2:48 pm
1:09 pm — 2:48 pm UA1564 United Airlines
Boston — Chicago
2h 39m
Find flight
from$171
2:42 pm — 6:24 pm
2:42 pm — 6:24 pm UA511 United Airlines
Boston — Chicago
4h 42m
Find flight
from$204
2:49 pm — 6:28 pm
2:49 pm — 6:28 pm UA511 United Airlines
Boston — Chicago
4h 39m
Find flight
from$648
3:30 pm — 5:07 pm
3:30 pm — 5:07 pm UA1598 United Airlines
Boston — Chicago
2h 37m
Find flight
from$171
4:22 pm — 6:14 pm
4:22 pm — 6:14 pm UA599 United Airlines
Boston — Chicago
2h 52m
Find flight
from$171
5:00 am — 6:37 am
5:00 am — 6:37 am UA203 United Airlines
Boston — Chicago
2h 37m
Find flight
from$130
6:33 pm — 8:22 pm
6:33 pm — 8:22 pm UA439 United Airlines
Boston — Chicago
2h 49m
Find flight
from$207
7:05 am — 8:50 am
7:05 am — 8:50 am UA449 United Airlines
Boston — Chicago
2h 45m
Find flight
from$75
7:15 am — 8:58 am
7:15 am — 8:58 am UA449 United Airlines
Boston — Chicago
2h 43m
Find flight
from$130
8:15 pm — 9:50 pm
8:15 pm — 9:50 pm UA714 United Airlines
Boston — Chicago
2h 35m
Find flight
from$130
8:35 am — 10:20 am
8:35 am — 10:20 am UA775 United Airlines
Boston — Chicago
2h 45m
Find flight
from$75
8:44 am — 10:24 am
8:44 am — 10:24 am UA775 United Airlines
Boston — Chicago
2h 40m
Find flight
from$130
10:40 am — 2:45 pm
10:40 am — 11:56 am UA2394 United Airlines
Boston — Newark
1h 24m stop
1:20 pm — 2:45 pm UA755 United Airlines
Newark — Chicago
5h 5m
including layover
Find flight
from$243
10:40 am — 4:39 pm
10:40 am — 11:56 am UA2394 United Airlines
Boston — Newark
3h 14m stop
3:10 pm — 4:39 pm UA743 United Airlines
Newark — Chicago
6h 59m
including layover
Find flight
from$243
10:40 am — 2:30 pm
10:40 am — 12:40 pm UA4336 United Airlines
Boston — Cleveland
1h 29m stop
2:09 pm — 2:30 pm UA1122 United Airlines
Cleveland — Chicago
4h 50m
including layover
Find flight
from$243
10:40 am — 4:56 pm
10:40 am — 12:40 pm UA4336 United Airlines
Boston — Cleveland
3h 40m stop
4:20 pm — 4:56 pm UA4206 United Airlines
Cleveland — Chicago
7h 16m
including layover
Find flight
from$280
10:40 am — 6:12 pm
10:40 am — 12:40 pm UA4336 United Airlines
Boston — Cleveland
5h stop
5:40 pm — 6:12 pm UA1704 United Airlines
Cleveland — Chicago
8h 32m
including layover
Find flight
from$355
10:40 am — 4:27 pm
10:40 am — 11:56 am UA2394 United Airlines
Boston — Newark
3h 4m stop
3:00 pm — 4:27 pm UA765 United Airlines
Newark — Chicago
6h 47m
including layover
Find flight
from$379
10:45 am — 5:50 pm
10:45 am — 12:02 pm UA2394 United Airlines
Boston — Newark
3h 58m stop
4:00 pm — 5:50 pm UA5905 United Airlines
Newark — Chicago
8h 5m
including layover
Find flight
from$379
10:45 am — 6:30 pm
10:45 am — 12:02 pm UA2394 United Airlines
Boston — Newark
4h 38m stop
4:40 pm — 6:30 pm UA5854 United Airlines
Newark — Chicago
8h 45m
including layover
Find flight
from$385
10:45 am — 6:31 pm
10:45 am — 12:02 pm UA2394 United Airlines
Boston — Newark
4h 58m stop
5:00 pm — 6:31 pm UA1180 United Airlines
Newark — Chicago
8h 46m
including layover
Find flight
from$499
11:00 am — 2:45 pm
11:00 am — 12:15 pm UA2394 United Airlines
Boston — Newark
1h 5m stop
1:20 pm — 2:45 pm UA755 United Airlines
Newark — Chicago
4h 45m
including layover
Find flight
from$240
11:40 am — 4:39 pm
11:40 am — 1:04 pm UA235 United Airlines
Boston — Newark
2h 6m stop
3:10 pm — 4:39 pm UA743 United Airlines
Newark — Chicago
5h 59m
including layover
Find flight
from$243
11:40 am — 6:31 pm
11:40 am — 1:04 pm UA235 United Airlines
Boston — Newark
3h 56m stop
5:00 pm — 6:31 pm UA1180 United Airlines
Newark — Chicago
7h 51m
including layover
Find flight
from$351
11:40 am — 6:20 pm
11:40 am — 1:04 pm UA235 United Airlines
Boston — Newark
3h 26m stop
4:30 pm — 6:20 pm UA5854 United Airlines
Newark — Chicago
7h 40m
including layover
Find flight
from$379
11:40 am — 6:36 pm
11:40 am — 1:04 pm UA235 United Airlines
Boston — Newark
3h 56m stop
5:00 pm — 6:36 pm UA2010 United Airlines
Newark — Chicago
7h 56m
including layover
Find flight
from$379
11:40 am — 7:52 pm
11:40 am — 1:04 pm UA235 United Airlines
Boston — Newark
5h 11m stop
6:15 pm — 7:52 pm UA1709 United Airlines
Newark — Chicago
9h 12m
including layover
Find flight
from$385
11:45 am — 6:37 pm
11:45 am — 1:09 pm UA695 United Airlines
Boston — Newark
3h 51m stop
5:00 pm — 6:37 pm UA2010 United Airlines
Newark — Chicago
7h 52m
including layover
Find flight
from$379
11:45 am — 6:20 pm
11:45 am — 1:09 pm UA695 United Airlines
Boston — Newark
3h 21m stop
4:30 pm — 6:20 pm UA5854 United Airlines
Newark — Chicago
7h 35m
including layover
Find flight
from$379
11:45 am — 7:36 pm
11:45 am — 1:09 pm UA695 United Airlines
Boston — Newark
4h 51m stop
6:00 pm — 7:36 pm UA1709 United Airlines
Newark — Chicago
8h 51m
including layover
Find flight
from$435
11:45 am — 4:39 pm
11:45 am — 1:09 pm UA695 United Airlines
Boston — Newark
2h 1m stop
3:10 pm — 4:39 pm UA743 United Airlines
Newark — Chicago
5h 54m
including layover
Find flight
from$437
11:45 am — 6:31 pm
11:45 am — 1:09 pm UA695 United Airlines
Boston — Newark
3h 51m stop
5:00 pm — 6:31 pm UA1180 United Airlines
Newark — Chicago
7h 46m
including layover
Find flight
from$600
12:05 pm — 10:22 am
+1 day
12:05 pm — 2:29 pm UA652 United Airlines
Boston — Denver
16h 31m stop
7:00 am — 10:22 am UA532 United Airlines
Denver — Chicago
23h 17m
including layover
Find flight
from$381
12:05 pm — 9:06 am
+1 day
12:05 pm — 2:29 pm UA652 United Airlines
Boston — Denver
15h 15m stop
5:44 am — 9:06 am UA1227 United Airlines
Denver — Chicago
22h 1m
including layover
Find flight
from$381
12:05 pm — 9:45 pm
12:05 pm — 2:29 pm UA652 United Airlines
Boston — Denver
3h 46m stop
6:15 pm — 9:45 pm UA254 United Airlines
Denver — Chicago
10h 40m
including layover
Find flight
from$384
12:05 pm — 8:19 pm
12:05 pm — 2:29 pm UA652 United Airlines
Boston — Denver
2h 24m stop
4:53 pm — 8:19 pm UA830 United Airlines
Denver — Chicago
9h 14m
including layover
Find flight
from$497
12:05 pm — 7:18 pm
12:05 pm — 2:29 pm UA652 United Airlines
Boston — Denver
1h 24m stop
3:53 pm — 7:18 pm UA478 United Airlines
Denver — Chicago
8h 13m
including layover
Find flight
from$497
12:05 pm — 11:12 pm
12:05 pm — 2:29 pm UA652 United Airlines
Boston — Denver
5h 26m stop
7:55 pm — 11:12 pm UA1150 United Airlines
Denver — Chicago
12h 7m
including layover
Find flight
from$599
2:01 pm — 10:20 pm
2:01 pm — 5:01 pm UA1772 United Airlines
Boston — Houston
2h 48m stop
7:49 pm — 10:20 pm UA2131 United Airlines
Houston — Chicago
9h 19m
including layover
Find flight
from$385
2:36 pm — 10:35 pm
2:36 pm — 4:00 pm UA1551 United Airlines
Boston — Newark
5h 10m stop
9:10 pm — 10:35 pm UA1249 United Airlines
Newark — Chicago
8h 59m
including layover
Find flight
from$385
2:36 pm — 6:45 am
+1 day
2:36 pm — 4:00 pm UA1551 United Airlines
Boston — Newark
13h 26m stop
5:26 am — 6:45 am UA2139 United Airlines
Newark — Chicago
17h 9m
including layover
Find flight
from$402
2:36 pm — 8:06 am
+1 day
2:36 pm — 4:00 pm UA1551 United Airlines
Boston — Newark
14h 36m stop
6:36 am — 8:06 am UA2001 United Airlines
Newark — Chicago
18h 30m
including layover
Find flight
from$402
2:36 pm — 8:38 pm
2:36 pm — 4:00 pm UA1551 United Airlines
Boston — Newark
3h 5m stop
7:05 pm — 8:38 pm UA693 United Airlines
Newark — Chicago
7h 2m
including layover
Find flight
from$414
2:36 pm — 9:32 pm
2:36 pm — 4:00 pm UA1551 United Airlines
Boston — Newark
4h 5m stop
8:05 pm — 9:32 pm UA556 United Airlines
Newark — Chicago
7h 56m
including layover
Find flight
from$420
2:36 pm — 9:31 pm
2:36 pm — 4:00 pm UA1551 United Airlines
Boston — Newark
4h 5m stop
8:05 pm — 9:31 pm UA1497 United Airlines
Newark — Chicago
7h 55m
including layover
Find flight
from$435
2:36 pm — 8:25 pm
2:36 pm — 4:00 pm UA1551 United Airlines
Boston — Newark
3h 1m stop
7:01 pm — 8:25 pm UA2015 United Airlines
Newark — Chicago
6h 49m
including layover
Find flight
from$466
2:36 pm — 6:31 pm
2:36 pm — 4:00 pm UA1551 United Airlines
Boston — Newark
1h stop
5:00 pm — 6:31 pm UA1180 United Airlines
Newark — Chicago
4h 55m
including layover
Find flight
from$519
3:40 pm — 11:22 pm
3:40 pm — 6:05 pm UA448 United Airlines
Boston — Denver
2h stop
8:05 pm — 11:22 pm UA1040 United Airlines
Denver — Chicago
8h 42m
including layover
Find flight
from$438
3:40 pm — 11:12 pm
3:40 pm — 6:05 pm UA448 United Airlines
Boston — Denver
1h 50m stop
7:55 pm — 11:12 pm UA1150 United Airlines
Denver — Chicago
8h 32m
including layover
Find flight
from$679
3:55 pm — 1:53 am
+1 day
3:55 pm — 7:15 pm UA351 United Airlines
Boston — San Francisco
35m stop
7:50 pm — 1:53 am UA1042 United Airlines
San Francisco — Chicago
10h 58m
including layover
Find flight
from$706
4:00 pm — 9:06 am
+1 day
4:00 pm — 6:00 pm UA4373 United Airlines
Boston — Cleveland
14h 45m stop
8:45 am — 9:06 am UA776 United Airlines
Cleveland — Chicago
18h 6m
including layover
Find flight
from$398
4:00 pm — 2:30 pm
+1 day
4:00 pm — 6:00 pm UA4373 United Airlines
Boston — Cleveland
20h 9m stop
2:09 pm — 2:30 pm UA1122 United Airlines
Cleveland — Chicago
23h 30m
including layover
Find flight
from$398
4:00 pm — 12:51 pm
+1 day
4:00 pm — 6:00 pm UA4373 United Airlines
Boston — Cleveland
18h 30m stop
12:30 pm — 12:51 pm UA1450 United Airlines
Cleveland — Chicago
21h 51m
including layover
Find flight
from$398
4:00 pm — 7:00 am
+1 day
4:00 pm — 6:00 pm UA4373 United Airlines
Boston — Cleveland
12h 39m stop
6:39 am — 7:00 am UA2116 United Airlines
Cleveland — Chicago
16h
including layover
Find flight
from$398
4:00 pm — 8:25 pm
4:00 pm — 6:00 pm UA4373 United Airlines
Boston — Cleveland
1h 40m stop
7:40 pm — 8:25 pm UA5250 United Airlines
Cleveland — Chicago
5h 25m
including layover
Find flight
from$473
4:00 pm — 8:16 pm
4:00 pm — 6:00 pm UA4373 United Airlines
Boston — Cleveland
1h 40m stop
7:40 pm — 8:16 pm UA3687 United Airlines
Cleveland — Chicago
5h 16m
including layover
Find flight
from$655
4:45 pm — 9:57 pm
4:45 pm — 6:10 pm UA1425 United Airlines
Boston — Newark
2h 18m stop
8:28 pm — 9:57 pm UA1611 United Airlines
Newark — Chicago
6h 12m
including layover
Find flight
from$445
4:45 pm — 10:35 pm
4:45 pm — 6:10 pm UA1425 United Airlines
Boston — Newark
3h stop
9:10 pm — 10:35 pm UA1249 United Airlines
Newark — Chicago
6h 50m
including layover
Find flight
from$536
4:45 pm — 8:25 pm
4:45 pm — 6:10 pm UA1425 United Airlines
Boston — Newark
51m stop
7:01 pm — 8:25 pm UA2015 United Airlines
Newark — Chicago
4h 40m
including layover
Find flight
from$653
5:30 am — 9:20 am
5:30 am — 6:43 am UA2077 United Airlines
Boston — Newark
1h 11m stop
7:54 am — 9:20 am UA977 United Airlines
Newark — Chicago
4h 50m
including layover
Find flight
from$243
5:30 am — 12:32 pm
5:30 am — 6:43 am UA2077 United Airlines
Boston — Newark
4h 17m stop
11:00 am — 12:32 pm UA1697 United Airlines
Newark — Chicago
8h 2m
including layover
Find flight
from$379
5:30 am — 11:32 am
5:30 am — 6:43 am UA2077 United Airlines
Boston — Newark
3h 17m stop
10:00 am — 11:32 am UA1953 United Airlines
Newark — Chicago
7h 2m
including layover
Find flight
from$379
5:40 am — 9:19 am
5:40 am — 7:10 am UA389 United Airlines
Boston — Washington D.C.
1h 9m stop
8:19 am — 9:19 am UA374 United Airlines
Washington D.C. — Chicago
4h 39m
including layover
Find flight
from$243
5:40 am — 11:42 am
5:40 am — 7:11 am UA389 United Airlines
Boston — Washington D.C.
3h 34m stop
10:45 am — 11:42 am UA721 United Airlines
Washington D.C. — Chicago
7h 2m
including layover
Find flight
from$243
5:40 am — 11:46 am
5:40 am — 7:11 am UA389 United Airlines
Boston — Washington D.C.
3h 34m stop
10:45 am — 11:46 am UA810 United Airlines
Washington D.C. — Chicago
7h 6m
including layover
Find flight
from$243
5:45 am — 12:40 pm
5:45 am — 8:40 am UA304 United Airlines
Boston — Houston
1h 20m stop
10:00 am — 12:40 pm UA1403 United Airlines
Houston — Chicago
7h 55m
including layover
Find flight
from$516
5:47 pm — 7:57 am
+1 day
5:47 pm — 8:44 pm UA2195 United Airlines
Boston — Houston
8h 26m stop
5:10 am — 7:57 am UA2005 United Airlines
Houston — Chicago
15h 10m
including layover
Find flight
from$415
5:47 pm — 0:26 am
+1 day
5:47 pm — 8:44 pm UA2195 United Airlines
Boston — Houston
1h 11m stop
9:55 pm — 0:26 am UA1854 United Airlines
Houston — Chicago
7h 39m
including layover
Find flight
from$434
5:47 pm — 5:00 pm
+1 day
5:47 pm — 8:44 pm UA2195 United Airlines
Boston — Houston
17h 36m stop
2:20 pm — 5:00 pm UA1256 United Airlines
Houston — Chicago
24h 13m
including layover
Find flight
from$440
5:47 pm — 2:29 pm
+1 day
5:47 pm — 8:44 pm UA2195 United Airlines
Boston — Houston
15h 11m stop
11:55 am — 2:29 pm UA1160 United Airlines
Houston — Chicago
21h 42m
including layover
Find flight
from$527
5:47 pm — 10:18 am
+1 day
5:47 pm — 8:44 pm UA2195 United Airlines
Boston — Houston
11h 1m stop
7:45 am — 10:18 am UA638 United Airlines
Houston — Chicago
17h 31m
including layover
Find flight
from$527
6:00 am — 11:39 am
6:00 am — 7:12 am UA2077 United Airlines
Boston — Newark
3h 3m stop
10:15 am — 11:39 am UA1818 United Airlines
Newark — Chicago
6h 39m
including layover
Find flight
from$243
6:00 am — 10:19 am
6:00 am — 7:12 am UA2077 United Airlines
Boston — Newark
1h 43m stop
8:55 am — 10:19 am UA426 United Airlines
Newark — Chicago
5h 19m
including layover
Find flight
from$243
6:00 pm — 10:25 pm
6:00 pm — 7:32 pm UA1202 United Airlines
Boston — Newark
1h 28m stop
9:00 pm — 10:25 pm UA1611 United Airlines
Newark — Chicago
5h 25m
including layover
Find flight
from$234
6:20 am — 11:39 am
6:20 am — 7:37 am UA1078 United Airlines
Boston — Newark
2h 38m stop
10:15 am — 11:39 am UA1818 United Airlines
Newark — Chicago
6h 19m
including layover
Find flight
from$243
6:20 am — 12:32 pm
6:20 am — 7:37 am UA1078 United Airlines
Boston — Newark
3h 23m stop
11:00 am — 12:32 pm UA1697 United Airlines
Newark — Chicago
7h 12m
including layover
Find flight
from$379
6:20 am — 1:13 pm
6:20 am — 8:48 am UA2214 United Airlines
Boston — Denver
57m stop
9:45 am — 1:13 pm UA2385 United Airlines
Denver — Chicago
7h 53m
including layover
Find flight
from$425
6:30 pm — 9:57 pm
6:30 pm — 7:56 pm UA1202 United Airlines
Boston — Newark
32m stop
8:28 pm — 9:57 pm UA1611 United Airlines
Newark — Chicago
4h 27m
including layover
Find flight
from$445
6:45 am — 10:19 am
6:45 am — 8:03 am UA1078 United Airlines
Boston — Newark
52m stop
8:55 am — 10:19 am UA426 United Airlines
Newark — Chicago
4h 34m
including layover
Find flight
from$243
6:45 am — 2:32 pm
6:45 am — 8:03 am UA1078 United Airlines
Boston — Newark
4h 57m stop
1:00 pm — 2:32 pm UA1478 United Airlines
Newark — Chicago
8h 47m
including layover
Find flight
from$385
6:45 am — 1:32 pm
6:45 am — 8:03 am UA1078 United Airlines
Boston — Newark
3h 57m stop
12:00 pm — 1:32 pm UA2202 United Airlines
Newark — Chicago
7h 47m
including layover
Find flight
from$385
7:00 pm — 6:39 am
+1 day
7:00 pm — 8:32 pm UA2047 United Airlines
Boston — Newark
8h 43m stop
5:15 am — 6:39 am UA2139 United Airlines
Newark — Chicago
12h 39m
including layover
Find flight
from$227
7:10 am — 11:39 am
7:10 am — 8:27 am UA2165 United Airlines
Boston — Newark
1h 48m stop
10:15 am — 11:39 am UA1818 United Airlines
Newark — Chicago
5h 29m
including layover
Find flight
from$243
7:10 am — 1:32 pm
7:10 am — 8:27 am UA2165 United Airlines
Boston — Newark
3h 33m stop
12:00 pm — 1:32 pm UA2202 United Airlines
Newark — Chicago
7h 22m
including layover
Find flight
from$379
7:10 am — 2:45 pm
7:10 am — 8:27 am UA2165 United Airlines
Boston — Newark
4h 53m stop
1:20 pm — 2:45 pm UA755 United Airlines
Newark — Chicago
8h 35m
including layover
Find flight
from$402
7:30 pm — 8:30 am
+1 day
7:30 pm — 8:56 pm UA2047 United Airlines
Boston — Newark
10h 4m stop
7:00 am — 8:30 am UA628 United Airlines
Newark — Chicago
14h
including layover
Find flight
from$412
7:30 pm — 8:06 am
+1 day
7:30 pm — 8:56 pm UA2047 United Airlines
Boston — Newark
9h 40m stop
6:36 am — 8:06 am UA2001 United Airlines
Newark — Chicago
13h 36m
including layover
Find flight
from$428
7:30 pm — 4:31 pm
+1 day
7:30 pm — 8:56 pm UA2047 United Airlines
Boston — Newark
18h 6m stop
3:02 pm — 4:31 pm UA743 United Airlines
Newark — Chicago
22h 1m
including layover
Find flight
from$428
7:30 pm — 9:06 am
+1 day
7:30 pm — 8:56 pm UA2047 United Airlines
Boston — Newark
10h 44m stop
7:40 am — 9:06 am UA977 United Airlines
Newark — Chicago
14h 36m
including layover
Find flight
from$433
7:39 pm — 11:06 pm
7:39 pm — 9:16 pm UA2136 United Airlines
Boston — Washington D.C.
1h stop
10:16 pm — 11:06 pm UA552 United Airlines
Washington D.C. — Chicago
4h 27m
including layover
Find flight
from$243
7:39 pm — 6:56 am
+1 day
7:39 pm — 9:16 pm UA2136 United Airlines
Boston — Washington D.C.
8h 44m stop
6:00 am — 6:56 am UA1271 United Airlines
Washington D.C. — Chicago
12h 17m
including layover
Find flight
from$432
7:39 pm — 8:33 am
+1 day
7:39 pm — 9:16 pm UA2136 United Airlines
Boston — Washington D.C.
10h 14m stop
7:30 am — 8:33 am UA531 United Airlines
Washington D.C. — Chicago
13h 54m
including layover
Find flight
from$432
7:39 pm — 9:20 am
+1 day
7:39 pm — 9:16 pm UA2136 United Airlines
Boston — Washington D.C.
11h 3m stop
8:19 am — 9:20 am UA374 United Airlines
Washington D.C. — Chicago
14h 41m
including layover
Find flight
from$432
7:39 pm — 7:03 am
+1 day
7:39 pm — 9:16 pm UA2136 United Airlines
Boston — Washington D.C.
8h 51m stop
6:07 am — 7:03 am UA2395 United Airlines
Washington D.C. — Chicago
12h 24m
including layover
Find flight
from$432
7:39 pm — 8:09 am
+1 day
7:39 pm — 9:16 pm UA2136 United Airlines
Boston — Washington D.C.
9h 44m stop
7:00 am — 8:09 am UA605 United Airlines
Washington D.C. — Chicago
13h 30m
including layover
Find flight
from$432
7:41 am — 4:18 pm
7:41 am — 10:10 am UA339 United Airlines
Boston — Denver
2h 37m stop
12:47 pm — 4:18 pm UA263 United Airlines
Denver — Chicago
9h 37m
including layover
Find flight
from$366
7:41 am — 2:49 pm
7:41 am — 10:10 am UA339 United Airlines
Boston — Denver
1h 15m stop
11:25 am — 2:49 pm UA533 United Airlines
Denver — Chicago
8h 8m
including layover
Find flight
from$412
7:45 am — 2:32 pm
7:45 am — 9:01 am UA2165 United Airlines
Boston — Newark
3h 59m stop
1:00 pm — 2:32 pm UA1478 United Airlines
Newark — Chicago
7h 47m
including layover
Find flight
from$385
7:50 am — 0:26 am
+1 day
7:50 am — 10:50 am UA1254 United Airlines
Boston — Houston
11h 5m stop
9:55 pm — 0:26 am UA1854 United Airlines
Houston — Chicago
17h 36m
including layover
Find flight
from$295
7:50 am — 7:57 am
+1 day
7:50 am — 10:50 am UA1254 United Airlines
Boston — Houston
18h 20m stop
5:10 am — 7:57 am UA2005 United Airlines
Houston — Chicago
25h 7m
including layover
Find flight
from$336
7:50 am — 2:29 pm
7:50 am — 10:50 am UA1254 United Airlines
Boston — Houston
1h 5m stop
11:55 am — 2:29 pm UA1160 United Airlines
Houston — Chicago
7h 39m
including layover
Find flight
from$548
8:06 pm — 7:00 am
+1 day
8:06 pm — 10:10 pm UA4159 United Airlines
Boston — Cleveland
8h 29m stop
6:39 am — 7:00 am UA219 United Airlines
Cleveland — Chicago
11h 54m
including layover
Find flight
from$344
8:06 pm — 11:16 am
+1 day
8:06 pm — 10:10 pm UA4159 United Airlines
Boston — Cleveland
12h 45m stop
10:55 am — 11:16 am UA785 United Airlines
Cleveland — Chicago
16h 10m
including layover
Find flight
from$344
8:06 pm — 7:31 am
+1 day
8:06 pm — 10:10 pm UA4159 United Airlines
Boston — Cleveland
9h stop
7:10 am — 7:31 am UA2116 United Airlines
Cleveland — Chicago
12h 25m
including layover
Find flight
from$344
8:06 pm — 9:06 am
+1 day
8:06 pm — 10:10 pm UA4159 United Airlines
Boston — Cleveland
10h 35m stop
8:45 am — 9:06 am UA776 United Airlines
Cleveland — Chicago
14h
including layover
Find flight
from$398
8:06 pm — 8:07 am
+1 day
8:06 pm — 10:10 pm UA4159 United Airlines
Boston — Cleveland
9h 31m stop
7:41 am — 8:07 am UA2069 United Airlines
Cleveland — Chicago
13h 1m
including layover
Find flight
from$398
8:06 pm — 10:51 am
+1 day
8:06 pm — 10:10 pm UA4159 United Airlines
Boston — Cleveland
12h 20m stop
10:30 am — 10:51 am UA5643 United Airlines
Cleveland — Chicago
15h 45m
including layover
Find flight
from$449
8:20 pm — 7:57 am
+1 day
8:20 pm — 11:21 pm UA646 United Airlines
Boston — Houston
5h 49m stop
5:10 am — 7:57 am UA2005 United Airlines
Houston — Chicago
12h 37m
including layover
Find flight
from$336
8:20 pm — 10:18 am
+1 day
8:20 pm — 11:21 pm UA646 United Airlines
Boston — Houston
8h 24m stop
7:45 am — 10:18 am UA638 United Airlines
Houston — Chicago
14h 58m
including layover
Find flight
from$460
8:45 am — 2:46 pm
8:45 am — 10:02 am UA700 United Airlines
Boston — Newark
3h 18m stop
1:20 pm — 2:46 pm UA755 United Airlines
Newark — Chicago
7h 1m
including layover
Find flight
from$243
8:45 am — 3:38 pm
8:45 am — 10:02 am UA700 United Airlines
Boston — Newark
4h 2m stop
2:04 pm — 3:38 pm UA3691 United Airlines
Newark — Chicago
7h 53m
including layover
Find flight
from$379
8:45 am — 5:50 pm
8:45 am — 10:02 am UA700 United Airlines
Boston — Newark
5h 58m stop
4:00 pm — 5:50 pm UA5905 United Airlines
Newark — Chicago
10h 5m
including layover
Find flight
from$385
8:45 am — 4:26 pm
8:45 am — 10:02 am UA700 United Airlines
Boston — Newark
4h 58m stop
3:00 pm — 4:26 pm UA765 United Airlines
Newark — Chicago
8h 41m
including layover
Find flight
from$385
8:45 am — 6:30 pm
8:45 am — 10:02 am UA700 United Airlines
Boston — Newark
6h 38m stop
4:40 pm — 6:30 pm UA5854 United Airlines
Newark — Chicago
10h 45m
including layover
Find flight
from$385
8:45 am — 9:32 pm
8:45 am — 10:02 am UA700 United Airlines
Boston — Newark
10h 3m stop
8:05 pm — 9:32 pm UA556 United Airlines
Newark — Chicago
13h 47m
including layover
Find flight
from$385
8:45 am — 8:37 pm
8:45 am — 10:02 am UA700 United Airlines
Boston — Newark
9h 3m stop
7:05 pm — 8:37 pm UA693 United Airlines
Newark — Chicago
12h 52m
including layover
Find flight
from$385
8:45 am — 4:38 pm
8:45 am — 10:02 am UA700 United Airlines
Boston — Newark
5h 7m stop
3:09 pm — 4:38 pm UA743 United Airlines
Newark — Chicago
8h 53m
including layover
Find flight
from$402
9:09 am — 9:06 am
+1 day
9:09 am — 11:37 am UA1752 United Airlines
Boston — Denver
18h 7m stop
5:44 am — 9:06 am UA1227 United Airlines
Denver — Chicago
24h 57m
including layover
Find flight
from$325
9:09 am — 4:26 pm
9:09 am — 11:37 am UA1752 United Airlines
Boston — Denver
1h 18m stop
12:55 pm — 4:26 pm UA263 United Airlines
Denver — Chicago
8h 17m
including layover
Find flight
from$366
9:12 am — 4:18 pm
9:12 am — 11:40 am UA1921 United Airlines
Boston — Denver
1h 7m stop
12:47 pm — 4:18 pm UA263 United Airlines
Denver — Chicago
8h 6m
including layover
Find flight
from$556
9:45 am — 2:46 pm
9:45 am — 11:01 am UA1928 United Airlines
Boston — Newark
2h 19m stop
1:20 pm — 2:46 pm UA755 United Airlines
Newark — Chicago
6h 1m
including layover
Find flight
from$243
9:45 am — 4:39 pm
9:45 am — 11:02 am UA1928 United Airlines
Boston — Newark
4h 8m stop
3:10 pm — 4:39 pm UA743 United Airlines
Newark — Chicago
7h 54m
including layover
Find flight
from$280
9:45 am — 4:27 pm
9:45 am — 11:02 am UA1928 United Airlines
Boston — Newark
3h 58m stop
3:00 pm — 4:27 pm UA765 United Airlines
Newark — Chicago
7h 42m
including layover
Find flight
from$379
9:45 am — 3:38 pm
9:45 am — 11:02 am UA1928 United Airlines
Boston — Newark
3h 2m stop
2:04 pm — 3:38 pm UA3691 United Airlines
Newark — Chicago
6h 53m
including layover
Find flight
from$379
9:47 am — 3:57 pm
9:47 am — 11:17 am UA525 United Airlines
Boston — Washington D.C.
3h 28m stop
2:45 pm — 3:57 pm UA5236 United Airlines
Washington D.C. — Chicago
7h 10m
including layover
Find flight
from$243
9:47 am — 1:33 pm
9:47 am — 11:17 am UA525 United Airlines
Boston — Washington D.C.
1h 18m stop
12:35 pm — 1:33 pm UA221 United Airlines
Washington D.C. — Chicago
4h 46m
including layover
Find flight
from$243
9:47 am — 5:07 pm
9:47 am — 11:17 am UA525 United Airlines
Boston — Washington D.C.
4h 28m stop
3:45 pm — 5:07 pm UA5250 United Airlines
Washington D.C. — Chicago
8h 20m
including layover
Find flight
from$434
5:40 am — 11:18 am
5:40 am — 7:11 am UA389 United Airlines
Boston — Washington D.C.
1h 14m stop
8:25 am — 9:51 am UA6130 United Airlines
Washington D.C. — Detroit
1h 4m stop
10:55 am — 11:18 am UA5958 United Airlines
Detroit — Chicago
6h 38m
including layover
Find flight
from$363
5:40 am — 12:32 pm
5:40 am — 7:10 am UA389 United Airlines
Boston — Washington D.C.
1h 15m stop
8:25 am — 9:46 am UA6255 United Airlines
Washington D.C. — New York
1h 14m stop
11:00 am — 12:32 pm UA1697 United Airlines
New York — Chicago
7h 52m
including layover
Find flight
from$373
6:00 am — 12:51 pm
6:00 am — 7:12 am UA2077 United Airlines
Boston — Newark
1h 47m stop
8:59 am — 10:31 am UA1530 United Airlines
Newark — Cleveland
1h 59m stop
12:30 pm — 12:51 pm UA1450 United Airlines
Cleveland — Chicago
7h 51m
including layover
Find flight
from$357
6:00 am — 2:30 pm
6:00 am — 7:12 am UA2077 United Airlines
Boston — Newark
1h 47m stop
8:59 am — 10:31 am UA1530 United Airlines
Newark — Cleveland
3h 38m stop
2:09 pm — 2:30 pm UA1122 United Airlines
Cleveland — Chicago
9h 30m
including layover
Find flight
from$357
8:06 pm — 9:20 am
+1 day
8:06 pm — 10:10 pm UA4159 United Airlines
Boston — Cleveland
7h 50m stop
6:00 am — 7:08 am UA623 United Airlines
Cleveland — Washington D.C.
1h 11m stop
8:19 am — 9:20 am UA374 United Airlines
Washington D.C. — Chicago
14h 14m
including layover
Find flight
from$342
8:45 am — 6:06 pm
8:45 am — 10:02 am UA700 United Airlines
Boston — Newark
2h 23m stop
12:25 pm — 2:22 pm DL4896 Delta Air Lines Inc.
Newark — Detroit
3h 28m stop
5:50 pm — 6:06 pm DL6183 Delta Air Lines Inc.
Detroit — Chicago
10h 21m
including layover
Find flight
from$530
*Departure and arrival times are local. Last updated on 05/23/2019

Flight Information

There are 15 flights by United Airlines from Boston to Chicago every week with departures from Logan, Boston City Heliport, Boston RT128 Rail, Boston South Rail. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:05 am to 9:47 am. Nonstop flight is 2h 35m. The time difference between Boston and Chicago is 1h.

  • The fastest flight 2h 35m
  • Average flight time 2h 43m
  • The earliest flight 10:05 am
  • The latest flight 9:47 am
  • Distance 852 ml

The cheapest months for traveling to Chicago are may, october, december.

The cheapest flight by United Airlines that our users were able to find is $75. This airfare is economy class on one-way UA449 flight for May 29, 2019 leaving Logan in Boston at 7:05 am, it includes all taxes and additional fees.

Find same flight?

Other Popular Airlines on the Route

Besides United Airlines there are other 3 airline carriers between Boston and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Boston to Chicago.

Nonstop flights

There are 22 direct flights every day from Boston. Airlines and fares are below:

See more direct flights

Connecting Flights

List of flights with layovers (1 and more stops):

See more connecting flights

How to book an air ticket yourself?

How to book an air 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 airfare.
  • 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.

Back