Flights from Boston to Chicago (BOS to ORD)

Discover more affordable routes and cheaper dates from Boston to Chicago (BOS to ORD) within a date range.

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US$120

8:39pm - 8:55am
Fri Aug 1st 2025

13h 16m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 Spirit Airlines · NK 1231 Depart at 8:39pm from Boston (BOS) Fly for 3h 36m Arrive at 12:15am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 6h 25m

Sat Aug 2nd 2025 Spirit Airlines · NK 1986 Depart at 6:40am from Fort Lauderdale (FLL) Fly for 3h 15m Arrive at 8:55am in Chicago (ORD)
US$124

6:07am - 8:05am
Fri Aug 1st 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 1414 Depart at 6:07am from Boston (BOS) Fly for 2h 58m Arrive at 8:05am in Chicago (ORD)
US$146

6:15am - 3:31pm
Fri Aug 1st 2025

10h 16m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 Spirit Airlines · NK 1449 Depart at 6:15am from Boston (BOS) Fly for 3h 24m Arrive at 9:39am in Orlando (MCO)

Layover in Orlando for 3h 44m

Fri Aug 1st 2025 Spirit Airlines · NK 1369 Depart at 1:23pm from Orlando (MCO) Fly for 3h 8m Arrive at 3:31pm in Chicago (ORD)
US$146

6:15am - 5:58pm
Fri Aug 1st 2025

12h 43m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 Spirit Airlines · NK 1449 Depart at 6:15am from Boston (BOS) Fly for 3h 24m Arrive at 9:39am in Orlando (MCO)

Layover in Orlando for 6h 10m

Fri Aug 1st 2025 Spirit Airlines · NK 1114 Depart at 3:49pm from Orlando (MCO) Fly for 3h 9m Arrive at 5:58pm in Chicago (ORD)
US$153

9:03am - 10:54am
Fri Aug 1st 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 600 Depart at 9:03am from Boston (BOS) Fly for 2h 51m Arrive at 10:54am in Chicago (ORD)
US$153

7:45am - 9:43am
Fri Aug 1st 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 1909 Depart at 7:45am from Boston (BOS) Fly for 2h 58m Arrive at 9:43am in Chicago (ORD)
US$168

10:40am - 12:31pm
Fri Aug 1st 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 788 Depart at 10:40am from Boston (BOS) Fly for 2h 51m Arrive at 12:31pm in Chicago (ORD)
US$168

8:20pm - 10:12pm
Fri Aug 1st 2025

2h 52m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 2229 Depart at 8:20pm from Boston (BOS) Fly for 2h 52m Arrive at 10:12pm in Chicago (ORD)
US$168

6:03pm - 8:00pm
Fri Aug 1st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 1015 Depart at 6:03pm from Boston (BOS) Fly for 2h 57m Arrive at 8:00pm in Chicago (ORD)
US$184

3:16pm - 5:05pm
Fri Aug 1st 2025

2h 49m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 1032 Depart at 3:16pm from Boston (BOS) Fly for 2h 49m Arrive at 5:05pm in Chicago (ORD)
US$201

4:27pm - 6:20pm
Fri Aug 1st 2025

2h 53m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 2040 Depart at 4:27pm from Boston (BOS) Fly for 2h 53m Arrive at 6:20pm in Chicago (ORD)
US$229

10:21am - 5:10pm
Fri Aug 1st 2025

7h 49m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 Spirit Airlines · NK 1837 Depart at 10:21am from Boston (BOS) Fly for 4h 10m Arrive at 1:31pm in Dallas (DFW)

Layover in Dallas for 1h 25m

Fri Aug 1st 2025 Spirit Airlines · NK 1634 Depart at 2:56pm from Dallas (DFW) Fly for 2h 14m Arrive at 5:10pm in Chicago (ORD)
US$232

5:30am - 9:43am
Fri Aug 1st 2025

5h 13m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1734 Depart at 5:30am from Boston (BOS) Fly for 1h 34m Arrive at 7:04am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 26m

Fri Aug 1st 2025 United Airlines · UA 2440 Depart at 8:30am from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 9:43am in Chicago (ORD)
US$236

12:00pm - 1:51pm
Fri Aug 1st 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 1732 Depart at 12:00pm from Boston (BOS) Fly for 2h 51m Arrive at 1:51pm in Chicago (ORD)
US$260

6:05am - 10:39am
Fri Aug 1st 2025

5h 34m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1833 Depart at 6:05am from Boston (BOS) Fly for 1h 22m Arrive at 7:27am in New York (EWR)

Layover in New York for 1h 33m

Fri Aug 1st 2025 United Airlines · UA 2337 Depart at 9:00am from New York (EWR) Fly for 2h 39m Arrive at 10:39am in Chicago (ORD)
US$260

8:39am - 1:14pm
Fri Aug 1st 2025

5h 35m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 515 Depart at 8:39am from Boston (BOS) Fly for 1h 20m Arrive at 9:59am in New York (EWR)

Layover in New York for 1h 38m

Fri Aug 1st 2025 United Airlines · UA 1875 Depart at 11:37am from New York (EWR) Fly for 2h 37m Arrive at 1:14pm in Chicago (ORD)
US$260

7:00am - 11:59am
Fri Aug 1st 2025

5h 59m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 570 Depart at 7:00am from Boston (BOS) Fly for 1h 22m Arrive at 8:22am in New York (EWR)

Layover in New York for 1h 58m

Fri Aug 1st 2025 United Airlines · UA 1525 Depart at 10:20am from New York (EWR) Fly for 2h 39m Arrive at 11:59am in Chicago (ORD)
US$260

6:05am - 11:59am
Fri Aug 1st 2025

6h 54m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1833 Depart at 6:05am from Boston (BOS) Fly for 1h 22m Arrive at 7:27am in New York (EWR)

Layover in New York for 2h 53m

Fri Aug 1st 2025 United Airlines · UA 1525 Depart at 10:20am from New York (EWR) Fly for 2h 39m Arrive at 11:59am in Chicago (ORD)
US$260

7:00am - 1:14pm
Fri Aug 1st 2025

7h 14m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 570 Depart at 7:00am from Boston (BOS) Fly for 1h 22m Arrive at 8:22am in New York (EWR)

Layover in New York for 3h 15m

Fri Aug 1st 2025 United Airlines · UA 1875 Depart at 11:37am from New York (EWR) Fly for 2h 37m Arrive at 1:14pm in Chicago (ORD)
US$260

8:39am - 2:55pm
Fri Aug 1st 2025

7h 16m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 515 Depart at 8:39am from Boston (BOS) Fly for 1h 20m Arrive at 9:59am in New York (EWR)

Layover in New York for 3h 19m

Fri Aug 1st 2025 United Airlines · UA 2180 Depart at 1:18pm from New York (EWR) Fly for 2h 37m Arrive at 2:55pm in Chicago (ORD)
US$295

8:02pm - 8:39am
Fri Aug 1st 2025

13h 37m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 562 Depart at 8:02pm from Boston (BOS) Fly for 1h 27m Arrive at 9:29pm in New York (EWR)

Layover in New York for 9h 31m

Sat Aug 2nd 2025 United Airlines · UA 2705 Depart at 7:00am from New York (EWR) Fly for 2h 39m Arrive at 8:39am in Chicago (ORD)
US$321

7:04pm - 11:41pm
Fri Aug 1st 2025

5h 37m
Boston (BOS) → Chicago (ORD)

Direct

Fri Aug 1st 2025 United Airlines · UA 1308 Depart at 7:04pm from Boston (BOS) Fly for 5h 37m Arrive at 11:41pm in Chicago (ORD)
US$325

8:02pm - 7:38am
Fri Aug 1st 2025

12h 36m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 562 Depart at 8:02pm from Boston (BOS) Fly for 1h 27m Arrive at 9:29pm in New York (EWR)

Layover in New York for 8h 31m

Sat Aug 2nd 2025 United Airlines · UA 2160 Depart at 6:00am from New York (EWR) Fly for 2h 38m Arrive at 7:38am in Chicago (ORD)
US$325

7:04pm - 7:38am
Fri Aug 1st 2025

13h 34m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1308 Depart at 7:04pm from Boston (BOS) Fly for 1h 26m Arrive at 8:30pm in New York (EWR)

Layover in New York for 9h 30m

Sat Aug 2nd 2025 United Airlines · UA 2160 Depart at 6:00am from New York (EWR) Fly for 2h 38m Arrive at 7:38am in Chicago (ORD)
US$325

8:39am - 11:41pm
Fri Aug 1st 2025

16h 2m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 515 Depart at 8:39am from Boston (BOS) Fly for 1h 20m Arrive at 9:59am in New York (EWR)

Layover in New York for 12h 0m

Fri Aug 1st 2025 United Airlines · UA 1308 Depart at 9:59pm from New York (EWR) Fly for 2h 42m Arrive at 11:41pm in Chicago (ORD)
US$325

7:00am - 11:41pm
Fri Aug 1st 2025

17h 41m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 570 Depart at 7:00am from Boston (BOS) Fly for 1h 22m Arrive at 8:22am in New York (EWR)

Layover in New York for 13h 37m

Fri Aug 1st 2025 United Airlines · UA 1308 Depart at 9:59pm from New York (EWR) Fly for 2h 42m Arrive at 11:41pm in Chicago (ORD)
US$325

6:05am - 11:41pm
Fri Aug 1st 2025

18h 36m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1833 Depart at 6:05am from Boston (BOS) Fly for 1h 22m Arrive at 7:27am in New York (EWR)

Layover in New York for 14h 32m

Fri Aug 1st 2025 United Airlines · UA 1308 Depart at 9:59pm from New York (EWR) Fly for 2h 42m Arrive at 11:41pm in Chicago (ORD)
US$356

7:04pm - 11:41pm
Fri Aug 1st 2025

5h 37m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1308 Depart at 7:04pm from Boston (BOS) Fly for 1h 26m Arrive at 8:30pm in New York (EWR)

Layover in New York for 1h 29m

Fri Aug 1st 2025 United Airlines · UA 1308 Depart at 9:59pm from New York (EWR) Fly for 2h 42m Arrive at 11:41pm in Chicago (ORD)
US$368

9:40am - 11:41pm
Fri Aug 1st 2025

15h 1m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1469 Depart at 9:40am from Boston (BOS) Fly for 1h 19m Arrive at 10:59am in New York (EWR)

Layover in New York for 11h 0m

Fri Aug 1st 2025 United Airlines · UA 1308 Depart at 9:59pm from New York (EWR) Fly for 2h 42m Arrive at 11:41pm in Chicago (ORD)
US$373

8:39am - 7:57pm
Fri Aug 1st 2025

12h 18m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 515 Depart at 8:39am from Boston (BOS) Fly for 1h 20m Arrive at 9:59am in New York (EWR)

Layover in New York for 8h 16m

Fri Aug 1st 2025 United Airlines · UA 254 Depart at 6:15pm from New York (EWR) Fly for 2h 42m Arrive at 7:57pm in Chicago (ORD)
US$373

7:00am - 7:57pm
Fri Aug 1st 2025

13h 57m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 570 Depart at 7:00am from Boston (BOS) Fly for 1h 22m Arrive at 8:22am in New York (EWR)

Layover in New York for 9h 53m

Fri Aug 1st 2025 United Airlines · UA 254 Depart at 6:15pm from New York (EWR) Fly for 2h 42m Arrive at 7:57pm in Chicago (ORD)
US$373

8:39am - 9:36pm
Fri Aug 1st 2025

13h 57m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 515 Depart at 8:39am from Boston (BOS) Fly for 1h 20m Arrive at 9:59am in New York (EWR)

Layover in New York for 9h 55m

Fri Aug 1st 2025 United Airlines · UA 546 Depart at 7:54pm from New York (EWR) Fly for 2h 42m Arrive at 9:36pm in Chicago (ORD)
US$373

6:05am - 7:57pm
Fri Aug 1st 2025

14h 52m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1833 Depart at 6:05am from Boston (BOS) Fly for 1h 22m Arrive at 7:27am in New York (EWR)

Layover in New York for 10h 48m

Fri Aug 1st 2025 United Airlines · UA 254 Depart at 6:15pm from New York (EWR) Fly for 2h 42m Arrive at 7:57pm in Chicago (ORD)
US$401

5:30am - 2:33pm
Fri Aug 1st 2025

10h 3m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1734 Depart at 5:30am from Boston (BOS) Fly for 1h 34m Arrive at 7:04am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 6h 16m

Fri Aug 1st 2025 United Airlines · UA 2331 Depart at 1:20pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 2:33pm in Chicago (ORD)
US$421

7:00am - 2:55pm
Fri Aug 1st 2025

8h 55m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 570 Depart at 7:00am from Boston (BOS) Fly for 1h 22m Arrive at 8:22am in New York (EWR)

Layover in New York for 4h 56m

Fri Aug 1st 2025 United Airlines · UA 2180 Depart at 1:18pm from New York (EWR) Fly for 2h 37m Arrive at 2:55pm in Chicago (ORD)
US$421

6:05am - 2:55pm
Fri Aug 1st 2025

9h 50m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1833 Depart at 6:05am from Boston (BOS) Fly for 1h 22m Arrive at 7:27am in New York (EWR)

Layover in New York for 5h 51m

Fri Aug 1st 2025 United Airlines · UA 2180 Depart at 1:18pm from New York (EWR) Fly for 2h 37m Arrive at 2:55pm in Chicago (ORD)
US$422

6:05am - 1:14pm
Fri Aug 1st 2025

8h 9m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1833 Depart at 6:05am from Boston (BOS) Fly for 1h 22m Arrive at 7:27am in New York (EWR)

Layover in New York for 4h 10m

Fri Aug 1st 2025 United Airlines · UA 1875 Depart at 11:37am from New York (EWR) Fly for 2h 37m Arrive at 1:14pm in Chicago (ORD)
US$422

8:39am - 5:10pm
Fri Aug 1st 2025

9h 31m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 515 Depart at 8:39am from Boston (BOS) Fly for 1h 20m Arrive at 9:59am in New York (EWR)

Layover in New York for 5h 26m

Fri Aug 1st 2025 United Airlines · UA 1144 Depart at 3:25pm from New York (EWR) Fly for 2h 45m Arrive at 5:10pm in Chicago (ORD)
US$443

7:12pm - 11:30pm
Fri Aug 1st 2025

5h 18m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 2136 Depart at 7:12pm from Boston (BOS) Fly for 1h 46m Arrive at 8:58pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 21m

Fri Aug 1st 2025 United Airlines · UA 1738 Depart at 10:19pm from Washington, D.C. (IAD) Fly for 2h 11m Arrive at 11:30pm in Chicago (ORD)
US$443

9:40am - 2:55pm
Fri Aug 1st 2025

6h 15m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 United Airlines · UA 1469 Depart at 9:40am from Boston (BOS) Fly for 1h 19m Arrive at 10:59am in New York (EWR)

Layover in New York for 2h 19m

Fri Aug 1st 2025 United Airlines · UA 2180 Depart at 1:18pm from New York (EWR) Fly for 2h 37m Arrive at 2:55pm in Chicago (ORD)
US$528

6:32pm - 5:40am
Fri Aug 1st 2025

12h 8m
Boston (BOS) → Chicago (ORD)

1 Stop

Fri Aug 1st 2025 Alaska Airlines · AS 819 Depart at 6:32pm from Boston (BOS) Fly for 6h 30m Arrive at 10:02pm in Seattle (SEA)

Layover in Seattle for 1h 38m

Fri Aug 1st 2025 Alaska Airlines · AS 328 Depart at 11:40pm from Seattle (SEA) Fly for 4h 0m Arrive at 5:40am in Chicago (ORD)

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@sarahbb1

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@eyupitsjohn

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Roaming Sonaa

@roamingsonaa

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Andy Travels

@andy_travels

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Travel With Bender

@travelwitbender

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Wesley Mergard

@travel.with.wes

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Flights from Boston to Chicago (BOS to ORD)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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