Nonstop flights from Chicago to Boston

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

ORDBOS

Routes

2 airport pairs

When they leave

Chicago time

5:45a9:41pFirst departure 5:45 AM, last 9:41 PM

18 in the morning, 5:45 AM to 11:35 AM, then 13 in the afternoon, 12:05 PM to 4:02 PM, then 10 in the evening, 5:23 PM to 9:41 PM.

Every flight

Earliest first

5:45 AM→9:00 AMMDW to BOSSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
6:00 AM→9:15 AMMDW to BOSSouthwest AirlinesBoeing 737Sat, Sun
6:00 AM→9:34 AMORD to BOSAmerican AirlinesBoeing 737Mon, Tue
6:05 AM→9:37 AMORD to BOSAmerican AirlinesBoeing 737Wed, Thu, Fri, Sat, Sun
6:05 AM→9:29 AMORD to BOSUnited AirlinesBoeing 737Mon, Tue, Wed, Thu, Fri, Sun
6:40 AM→9:55 AMMDW to BOSSouthwest AirlinesBoeing 737Tue, Wed
6:54 AM→10:28 AMORD to BOSAmerican AirlinesBoeing 737Mon, Tue
7:00 AM→10:32 AMORD to BOSAmerican AirlinesBoeing 737Wed, Thu, Fri, Sat, Sun
7:33 AM→11:05 AMORD to BOSUnited AirlinesBoeing 737Daily
7:55 AM→11:25 AMMDW to BOSSouthwest AirlinesBoeing 737Sun
7:55 AM→11:24 AMORD to BOSDelta Air LinesAirbus A220-300Daily
8:15 AM→11:40 AMMDW to BOSSouthwest AirlinesBoeing 737Mon, Tue, Wed, Thu, Fri, Sat
8:26 AM→12:02 PMORD to BOSAmerican AirlinesEmbraer 175Wed, Thu, Fri, Sat, Sun
8:30 AM→12:07 PMORD to BOSAmerican AirlinesEmbraer 175Mon, Tue
9:15 AM→12:57 PMORD to BOSUnited AirlinesBoeing 737Daily
10:30 AM→2:07 PMORD to BOSUnited AirlinesBoeing 737 MAX 9Daily
10:30 AM→1:59 PMORD to BOSDelta Air LinesBoeing 737Daily
10:35 AM→2:13 PMORD to BOSAmerican AirlinesBoeing 737Mon, Tue
10:56 AM→2:23 PMORD to BOSJetBlueAirbus A220-300Daily
11:25 AM→2:45 PMMDW to BOSSouthwest AirlinesBoeing 737-700Sat
11:30 AM→3:03 PMORD to BOSAmerican AirlinesBoeing 737Wed, Thu, Fri, Sat, Sun
11:35 AM→2:55 PMMDW to BOSSouthwest AirlinesBoeing 737-700Mon, Thu, Fri
12:05 PM→3:25 PMMDW to BOSSouthwest AirlinesBoeing 737 MAX 8Sun
12:50 PM→4:10 PMMDW to BOSSouthwest AirlinesBoeing 737Tue, Wed
12:53 PM→4:29 PMORD to BOSUnited AirlinesBoeing 737Daily
1:54 PM→5:34 PMORD to BOSAmerican AirlinesBoeing 737Daily
1:55 PM→5:31 PMORD to BOSUnited AirlinesAirbus A321neoDaily
1:57 PM→5:36 PMORD to BOSAmerican AirlinesBoeing 737Mon, Tue
2:35 PM→5:55 PMMDW to BOSSouthwest AirlinesBoeing 737-700Mon, Tue, Wed, Thu, Fri
3:00 PM→6:40 PMORD to BOSAmerican AirlinesBoeing 737Wed, Thu, Fri, Sat, Sun
3:10 PM→6:30 PMMDW to BOSSouthwest AirlinesBoeing 737 MAX 8Sat, Sun
3:19 PM→6:59 PMORD to BOSDelta Air LinesAirbus A319Mon, Tue, Wed, Thu, Fri, Sun
3:55 PM→7:30 PMORD to BOSUnited AirlinesBoeing 737Daily
4:00 PM→7:50 PMORD to BOSAmerican AirlinesEmbraer 175Wed, Thu, Fri, Sat, Sun
4:02 PM→7:53 PMORD to BOSAmerican AirlinesEmbraer 175Mon, Tue
5:23 PM→9:00 PMORD to BOSAmerican AirlinesBoeing 737Daily
5:55 PM→9:20 PMMDW to BOSSouthwest AirlinesBoeing 737-700Sun
6:20 PM→9:56 PMORD to BOSUnited AirlinesAirbus A321neoDaily
6:30 PM→9:50 PMMDW to BOSSouthwest AirlinesBoeing 737-700Mon, Thu, Fri
7:15 PM→10:50 PMORD to BOSAmerican AirlinesBoeing 737Daily
7:30 PM→11:02 PMORD to BOSDelta Air LinesAirbus A319Daily
7:45 PM→11:21 PMORD to BOSUnited AirlinesBoeing 737 MAX 9Daily
8:20 PM→11:51 PMORD to BOSJetBlueAirbus A220-300Mon, Tue, Wed, Thu, Fri, Sun
8:30 PM→11:59 PMORD to BOSAmerican AirlinesBoeing 737Daily
9:41 PM→1:14 AM⁺¹ORD to BOSUnited AirlinesAirbus A321neoDaily

Schedules last checked Sep 19, 2026. Times are local.

Flying from Chicago to Boston

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

Flights run every day of the week, from 27 on Saturdays to 31 on Mondays, Thursdays, Fridays and Sundays. The first arrival in Boston is at 9:00 AM and the last at 1:14 AM the next day.

ORD to BOS is the busiest airport pair, with 179 flights a week, then MDW to BOS with 32.

Flying back, Boston to Chicago has 212 nonstop flights a week.

Return flights

Boston to ChicagoView

Find the cheapest day to fly from Chicago to Boston.

Schedules as of Oct 9, 2026.