Nonstop flights from Boston to Chicago

5 airlines fly from Boston (BOS) to 2 Chicago airports (ORD and MDW), with up to 31 flights a day.

BOSORD

Routes

2 airport pairs

When they leave

Boston time

6:01a9:05pFirst departure 6:01 AM, last 9:05 PM

15 in the morning, 6:01 AM to 11:58 AM, then 12 in the afternoon, 12:25 PM to 4:16 PM, then 11 in the evening, 5:01 PM to 9:05 PM.

Every flight

Earliest first

6:01 AM→8:00 AMBOS to ORDUnited AirlinesBoeing 737 MAX 9Daily
6:14 AM→8:20 AMBOS to ORDAmerican AirlinesBoeing 737Daily
7:05 AM→9:04 AMBOS to ORDUnited AirlinesAirbus A321neoDaily
7:10 AM→9:16 AMBOS to ORDAmerican AirlinesBoeing 737-800Daily
7:30 AM→9:26 AMBOS to ORDDelta Air LinesBoeing 737-800Daily
7:30 AM→9:05 AMBOS to MDWSouthwest AirlinesBoeing 737 MAX 8Daily
8:05 AM→10:04 AMBOS to ORDUnited AirlinesBoeing 737Daily
8:15 AM→10:11 AMBOS to ORDJetBlueAirbus A220-300Daily
8:27 AM→10:30 AMBOS to ORDAmerican AirlinesBoeing 737Daily
8:40 AM→10:15 AMBOS to MDWSouthwest AirlinesBoeing 737 MAX 8Sat
9:00 AM→10:56 AMBOS to ORDUnited AirlinesAirbus A321neoDaily
9:25 AM→11:00 AMBOS to MDWSouthwest AirlinesBoeing 737 MAX 8Sun
10:05 AM→11:35 AMBOS to MDWSouthwest AirlinesBoeing 737-700Tue, Wed
10:28 AM→12:29 PMBOS to ORDAmerican AirlinesBoeing 737Daily
10:38 AM→12:29 PMBOS to ORDUnited AirlinesBoeing 737 MAX 8Daily
11:58 AM→1:59 PMBOS to ORDAmerican AirlinesBoeing 737Daily
12:25 PM→2:19 PMBOS to ORDDelta Air LinesAirbus A319Mon, Tue, Wed, Thu, Fri, Sun
12:27 PM→2:20 PMBOS to ORDUnited AirlinesBoeing 737Daily
12:40 PM→2:10 PMBOS to MDWSouthwest AirlinesBoeing 737Mon, Thu, Fri
1:00 PM→2:35 PMBOS to MDWSouthwest AirlinesBoeing 737-700Sat
1:01 PM→3:15 PMBOS to ORDAmerican AirlinesEmbraer 175Daily
1:55 PM→3:25 PMBOS to MDWSouthwest AirlinesBoeing 737 MAX 8Sun
2:00 PM→4:05 PMBOS to ORDAmerican AirlinesEmbraer 175Daily
3:25 PM→5:00 PMBOS to MDWSouthwest AirlinesBoeing 737-700Sat
3:30 PM→5:22 PMBOS to ORDUnited AirlinesBoeing 737Daily
3:53 PM→6:04 PMBOS to ORDAmerican AirlinesBoeing 737Daily
3:55 PM→5:30 PMBOS to MDWSouthwest AirlinesBoeing 737Mon, Tue, Wed, Thu, Fri
4:16 PM→6:20 PMBOS to ORDDelta Air LinesAirbus A319Daily
5:01 PM→7:00 PMBOS to ORDUnited AirlinesBoeing 737 MAX 9Daily
5:21 PM→7:27 PMBOS to ORDJetBlueAirbus A220-300Mon, Tue, Wed, Thu, Fri, Sun
5:35 PM→7:15 PMBOS to MDWSouthwest AirlinesBoeing 737 MAX 8Sun
5:45 PM→8:04 PMBOS to ORDAmerican AirlinesBoeing 737Daily
6:40 PM→8:20 PMBOS to MDWSouthwest AirlinesBoeing 737-700Mon, Tue, Wed, Thu, Fri
6:42 PM→8:40 PMBOS to ORDUnited AirlinesBoeing 737 MAX 9Daily
7:17 PM→9:35 PMBOS to ORDAmerican AirlinesBoeing 737Daily
8:20 PM→10:00 PMBOS to MDWSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
8:31 PM→10:30 PMBOS to ORDUnited AirlinesBoeing 737Daily
8:50 PM→10:44 PMBOS to ORDDelta Air LinesAirbus A220-300Daily
9:05 PM→10:40 PMBOS to MDWSouthwest AirlinesBoeing 737Sun

Schedules last checked Sep 22, 2026. Times are local.

Flying from Boston to Chicago

American Airlines flies 10 times a day on the Boeing 737, Embraer 175 and Boeing 737-800. United Airlines flies 10 times a day on the Boeing 737, Boeing 737 MAX 9, Airbus A321neo and Boeing 737 MAX 8. Southwest Airlines flies 4 to 5 times a day on the Boeing 737 MAX 8, Boeing 737-700 and Boeing 737. Delta Air Lines flies 3 to 4 times a day on the Airbus A319, Airbus A220-300 and Boeing 737-800. JetBlue flies 1 to 2 times a day on the Airbus A220-300.

Flights run every day of the week, from 28 on Saturdays to 31 on Mondays, Thursdays, Fridays and Sundays. The first arrival in Chicago is at 8:00 AM and the last at 10:44 PM.

BOS to ORD is the busiest airport pair, with 180 flights a week, then BOS to MDW with 32.

Flying back, Chicago to Boston has 211 nonstop flights a week.

Return flights

Chicago to BostonView

Find the cheapest day to fly from Boston to Chicago.

Schedules as of Oct 9, 2026.