How to get to Chicago, IL, USA from New England by flight ? You can check flights from New England to Chicago, IL, USA below.
You can find flight ticket prices from New England to Chicago, IL, USA with our flight tickets search tool below
You take a bus, shuttle or taxi from your location in New England to Portland.
You take a flight from Portland to Chicago O'Hare and cost approximately 220 USD.
You take a bus, shuttle or taxi from Chicago O'Hare to your destination in Chicago, IL, USA.
Flight | Depart | Arrive | |
---|---|---|---|
DL5646
Delta
DL2735
Delta
|
05:35
Portland
09:55
Detroit
|
07:55
Detroit
10:26
Chicago O'Hare
|
Connect |
WN827
Southwest Airlines
WN1255 2612
Southwest Airlines
|
06:00
Portland
09:35
Baltimore
|
07:35
Baltimore
10:40
Chicago O'Hare
|
Connect |
AA752
American Airlines
AA2080
American Airlines
|
06:00
Portland
09:50
Charlotte
|
08:24
Charlotte
11:10
Chicago O'Hare
|
Connect |
AA4564
American Airlines
AA1167
American Airlines
|
06:00
Portland
09:59
Reagan Washington
|
07:52
Reagan Washington
11:10
Chicago O'Hare
|
Connect |
UA4814
United Airlines
UA1660
United Airlines
|
06:03
Portland
08:30
Newark
|
07:30
Newark
10:24
Chicago O'Hare
|
Connect |
AA6060
American Airlines
AA2095
American Airlines
|
06:04
Portland
09:15
Philadelphia
|
07:39
Philadelphia
10:50
Chicago O'Hare
|
Connect |
DL5404
Delta
DL696
Delta
|
06:25
Portland
09:10
New York La Guardia
|
08:05
New York La Guardia
10:57
Chicago O'Hare
|
Connect |
AA3732
American Airlines
|
07:05
Portland
|
08:57 Chicago O'Hare | Direct |
9K7261
Cape Air
AA1239
American Airlines
|
07:15
Portland
09:00
Boston
|
08:08
Boston
10:51
Chicago O'Hare
|
Connect |
UA3553
United Airlines
|
07:20
Portland
|
09:17 Chicago O'Hare | Direct |
UA4960
United Airlines
UA2413
United Airlines
|
07:50
Portland
10:58
Washington Dulles
|
09:42
Washington Dulles
12:01
Chicago O'Hare
|
Connect |
9K7281
Cape Air
AA1287
American Airlines
|
09:47
Portland
12:25
Boston
|
10:40
Boston
14:19
Chicago O'Hare
|
Connect |
UA4816
United Airlines
UA1651
United Airlines
|
10:33
Portland
13:20
Newark
|
12:08
Newark
14:55
Chicago O'Hare
|
Connect |
AA1884
American Airlines
AA1577
American Airlines
|
10:58
Portland
13:50
Philadelphia
|
12:30
Philadelphia
15:30
Chicago O'Hare
|
Connect |
UA4395
United Airlines
UA3579
United Airlines
|
12:10
Portland
16:18
Cleveland
|
14:02
Cleveland
16:57
Chicago O'Hare
|
Connect |
UA4817
United Airlines
UA2193
United Airlines
|
12:20
Portland
14:59
Newark
|
14:04
Newark
16:46
Chicago O'Hare
|
Connect |
AA3927
American Airlines
|
12:32
Portland
|
14:19 Chicago O'Hare | Direct |
DL4795
Delta
DL1211
Delta
|
12:36
Portland
15:10
New York La Guardia
|
14:06
New York La Guardia
16:53
Chicago O'Hare
|
Connect |
DL4795
Delta
DL1361
Delta
|
12:36
Portland
16:10
New York La Guardia
|
14:06
New York La Guardia
17:50
Chicago O'Hare
|
Connect |
WN3160
Southwest Airlines
WN2654
Southwest Airlines
|
12:45
Portland
15:10
Baltimore
|
14:15
Baltimore
16:15
Chicago O'Hare
|
Connect |
UA3463
United Airlines
|
13:10
Portland
|
14:50 Chicago O'Hare | Direct |
AA4589
American Airlines
AA2784
American Airlines
|
14:05
Portland
17:45
Reagan Washington
|
15:57
Reagan Washington
19:17
Chicago O'Hare
|
Connect |
UA6149
United Airlines
UA2608
United Airlines
|
14:45
Portland
17:15
Washington Dulles
|
16:25
Washington Dulles
18:33
Chicago O'Hare
|
Connect |
AA5195
American Airlines
AA490
American Airlines
|
15:13
Portland
17:55
Philadelphia
|
16:49
Philadelphia
19:40
Chicago O'Hare
|
Connect |
UA4819
United Airlines
UA1672
United Airlines
|
15:16
Portland
18:25
Newark
|
17:00
Newark
20:12
Chicago O'Hare
|
Connect |
9K7321
Cape Air
AA2293
American Airlines
|
16:05
Portland
19:25
Boston
|
16:58
Boston
21:25
Chicago O'Hare
|
Connect |
UA4550
United Airlines
UA5891
United Airlines
|
16:15
Portland
19:30
Pittsburgh
|
18:06
Pittsburgh
20:12
Chicago O'Hare
|
Connect |
DL4848
Delta
DL519
Delta
|
16:27
Portland
19:10
New York La Guardia
|
17:58
New York La Guardia
20:56
Chicago O'Hare
|
Connect |
UA4394
United Airlines
UA3627
United Airlines
|
16:40
Portland
19:45
Columbus
|
18:51
Columbus
20:15
Chicago O'Hare
|
Connect |
UA3491
United Airlines
|
16:51
Portland
|
18:48 Chicago O'Hare | Direct |
DL5474
Delta
DL4669
Delta
|
17:00
Portland
20:00
New York JFK
|
18:33
New York JFK
21:59
Chicago O'Hare
|
Connect |
AA4503
American Airlines
AA2679
American Airlines
|
17:08
Portland
21:00
Reagan Washington
|
19:00
Reagan Washington
22:10
Chicago O'Hare
|
Connect |
DL5654
Delta
DL2663
Delta
|
17:10
Portland
20:21
Detroit
|
19:20
Detroit
20:57
Chicago O'Hare
|
Connect |
AA4279
American Airlines
|
17:45
Portland
|
19:36 Chicago O'Hare | Direct |
AA6189
American Airlines
AA1680
American Airlines
|
18:25
Portland
21:30
Philadelphia
|
20:00
Philadelphia
23:01
Chicago O'Hare
|
Connect |
AA4539
American Airlines
AA774
American Airlines
|
18:30
Portland
22:00
New York La Guardia
|
19:59
New York La Guardia
23:31
Chicago O'Hare
|
Connect |
You take a bus, shuttle or taxi from your location in New England to Portland.
You take a flight from Portland to Chicago Midway and cost approximately 437 USD.
You take a bus, shuttle or taxi from Chicago Midway to your destination in Chicago, IL, USA.
Flight | Depart | Arrive | |
---|---|---|---|
WN827
Southwest Airlines
WN441
Southwest Airlines
|
06:00
Portland
09:25
Baltimore
|
07:35
Baltimore
10:25
Chicago Midway
|
Connect |
WN3160
Southwest Airlines
WN4354
Southwest Airlines
|
12:45
Portland
16:30
Baltimore
|
14:15
Baltimore
17:30
Chicago Midway
|
Connect |
DL5666
Delta
DL5014
Delta
|
12:48
Portland
15:55
Detroit
|
15:03
Detroit
16:24
Chicago Midway
|
Connect |
WN1436
Southwest Airlines
WN397
Southwest Airlines
|
13:05
Portland
16:50
Baltimore
|
14:35
Baltimore
17:50
Chicago Midway
|
Connect |
WN4447
Southwest Airlines
|
15:20
Portland
|
17:00 Chicago Midway | Direct |
WN2643
Southwest Airlines
WN3122
Southwest Airlines
|
16:20
Portland
18:50
Baltimore
|
17:55
Baltimore
19:50
Chicago Midway
|
Connect |
WN4443
Southwest Airlines
|
17:25
Portland
|
19:05 Chicago Midway | Direct |
WN4445
Southwest Airlines
|
17:30
Portland
|
19:10 Chicago Midway | Direct |
You take a bus, shuttle or taxi from your location in New England to Boston.
You take a flight from Boston to Chicago Midway and cost approximately 200 USD.
You take a bus, shuttle or taxi from Chicago Midway to your destination in Chicago, IL, USA.
Flight | Depart | Arrive | |
---|---|---|---|
WN345
Southwest Airlines
|
05:20
Boston
|
07:00 Chicago Midway | Direct |
WN2147
Southwest Airlines
|
05:30
Boston
|
07:10 Chicago Midway | Direct |
WN493
Southwest Airlines
WN441
Southwest Airlines
|
05:30
Boston
09:25
Baltimore
|
07:00
Baltimore
10:25
Chicago Midway
|
Connect |
WN493
Southwest Airlines
WN2778
Southwest Airlines
|
05:30
Boston
08:05
Baltimore
|
07:00
Baltimore
09:05
Chicago Midway
|
Connect |
WN4349
Southwest Airlines
WN334
Southwest Airlines
|
05:40
Boston
08:10
Baltimore
|
07:10
Baltimore
09:10
Chicago Midway
|
Connect |
WN959
Southwest Airlines
WN479
Southwest Airlines
|
06:00
Boston
08:50
Nashville
|
07:50
Nashville
10:20
Chicago Midway
|
Connect |
PD936
Porter Airlines
PD389
Porter Airlines
|
06:25
Boston
10:15
Billy Bishop Toronto City
|
08:24
Billy Bishop Toronto City
11:02
Chicago Midway
|
Connect |
PD936
Porter Airlines
PD387
Porter Airlines
|
06:25
Boston
10:45
Billy Bishop Toronto City
|
08:24
Billy Bishop Toronto City
11:32
Chicago Midway
|
Connect |
WN2791
Southwest Airlines
WN441
Southwest Airlines
|
06:30
Boston
09:25
Baltimore
|
08:10
Baltimore
10:25
Chicago Midway
|
Connect |
DL1457
Delta
DL2153
Delta
|
07:00
Boston
11:05
Atlanta
|
10:05
Atlanta
11:59
Chicago Midway
|
Connect |
PD938
Porter Airlines
PD389
Porter Airlines
|
08:35
Boston
11:35
Billy Bishop Toronto City
|
10:34
Billy Bishop Toronto City
12:20
Chicago Midway
|
Connect |
WN402
Southwest Airlines
WN774
Southwest Airlines
|
08:45
Boston
12:15
Baltimore
|
10:20
Baltimore
13:15
Chicago Midway
|
Connect |
DL1610
Delta
DL4777
Delta
|
08:55
Boston
12:10
Detroit
|
11:14
Detroit
12:35
Chicago Midway
|
Connect |
WN1383
Southwest Airlines
WN774
Southwest Airlines
|
09:45
Boston
12:15
Baltimore
|
11:20
Baltimore
13:15
Chicago Midway
|
Connect |
DL2295
Delta
DL2640
Delta
|
10:00
Boston
14:23
Atlanta
|
13:01
Atlanta
15:15
Chicago Midway
|
Connect |
WN270
Southwest Airlines
|
10:15
Boston
|
12:05 Chicago Midway | Direct |
WN1223
Southwest Airlines
|
10:45
Boston
|
12:25 Chicago Midway | Direct |
PD940
Porter Airlines
PD393
Porter Airlines
|
11:20
Boston
15:15
Billy Bishop Toronto City
|
13:19
Billy Bishop Toronto City
16:02
Chicago Midway
|
Connect |
DL1497
Delta
DL2190
Delta
|
12:18
Boston
16:20
Atlanta
|
15:20
Atlanta
17:16
Chicago Midway
|
Connect |
WN3080
Southwest Airlines
WN397
Southwest Airlines
|
12:30
Boston
16:50
Baltimore
|
14:05
Baltimore
17:50
Chicago Midway
|
Connect |
WN2176
Southwest Airlines
WN4354
Southwest Airlines
|
12:35
Boston
16:30
Baltimore
|
14:10
Baltimore
17:30
Chicago Midway
|
Connect |
WN885
Southwest Airlines
|
13:10
Boston
|
14:55 Chicago Midway | Direct |
PD942
Porter Airlines
PD395
Porter Airlines
|
13:30
Boston
16:35
Billy Bishop Toronto City
|
15:29
Billy Bishop Toronto City
17:22
Chicago Midway
|
Connect |
WN2078
Southwest Airlines
|
13:35
Boston
|
15:20 Chicago Midway | Direct |
WN1379
Southwest Airlines
WN397
Southwest Airlines
|
13:45
Boston
16:50
Baltimore
|
15:20
Baltimore
17:50
Chicago Midway
|
Connect |
WN3419
Southwest Airlines
WN3419
Southwest Airlines
|
14:00
Boston
16:50
St. Louis
|
16:00
St. Louis
17:55
Chicago Midway
|
Connect |
DL1644
Delta
DL5094
Delta
|
14:38
Boston
18:13
Detroit
|
16:56
Detroit
18:39
Chicago Midway
|
Connect |
WN3687
Southwest Airlines
|
15:25
Boston
|
17:05 Chicago Midway | Direct |
WN3016
Southwest Airlines
WN2916
Southwest Airlines
|
15:45
Boston
19:15
Nashville
|
17:30
Nashville
20:45
Chicago Midway
|
Connect |
WN1216
Southwest Airlines
WN3990
Southwest Airlines
|
16:55
Boston
21:00
Baltimore
|
18:35
Baltimore
22:00
Chicago Midway
|
Connect |
WN409
Southwest Airlines
WN3478
Southwest Airlines
|
17:40
Boston
20:50
Nashville
|
19:35
Nashville
22:20
Chicago Midway
|
Connect |
WN1399
Southwest Airlines
|
18:10
Boston
|
20:00 Chicago Midway | Direct |
WN2461
Southwest Airlines
WN687
Southwest Airlines
|
18:50
Boston
22:05
Baltimore
|
20:35
Baltimore
23:05
Chicago Midway
|
Connect |
You can find hotels and accommodations in Chicago, IL, USA with our hotels search tool below
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