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BOS → ORD08 May 2026Live inventory
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Showing 25
of 123
live flights
Delta Air Lines
DL-2570
07:35
05/08/2026
BOS
Boston Airport
1h 52m
Non-stop
09:27
05/08/2026
ORD
Chicago Airport
₹8,061
per person
✕ Non-refundable3 fare options
Delta Air Lines
DL-2804
20:40
05/08/2026
BOS
Boston Airport
1h 55m
Non-stop
22:35
05/08/2026
ORD
Chicago Airport
₹8,061
per person
✕ Non-refundable3 fare options
Delta Air Lines
DL-2646
16:15
05/08/2026
BOS
Boston Airport
2h 0m
Non-stop
18:15
05/08/2026
ORD
Chicago Airport
₹8,061
per person
✕ Non-refundable3 fare options
American Airlines
AA-1509
06:30
05/08/2026
BOS
Boston Airport
2h 14m
Non-stop
08:44
05/08/2026
ORD
Chicago Airport
₹8,184
per person
✕ Non-refundable14 fare options
American Airlines
AA-425
19:50
05/08/2026
BOS
Boston Airport
2h 10m
Non-stop
22:00
05/08/2026
ORD
Chicago Airport
₹8,184
per person
✕ Non-refundable9 fare options
American Airlines
AA-3209
15:16
05/08/2026
BOS
Boston Airport
2h 14m
Non-stop
17:30
05/08/2026
ORD
Chicago Airport
₹8,184
per person
✕ Non-refundable9 fare options
American Airlines
AA-2390
15:59
05/08/2026
BOS
Boston Airport
2h 14m
Non-stop
18:13
05/08/2026
ORD
Chicago Airport
₹8,184
per person
✕ Non-refundable9 fare options
American Airlines
AA-1040
16:32
05/08/2026
BOS
Boston Airport
2h 17m
Non-stop
18:49
05/08/2026
ORD
Chicago Airport
₹8,184
per person
✕ Non-refundable9 fare options
American Airlines
AA-2815
17:35
05/08/2026
BOS
Boston Airport
2h 17m
Non-stop
19:52
05/08/2026
ORD
Chicago Airport
₹8,184
per person
✕ Non-refundable9 fare options
American Airlines
AA-1009
18:52
05/08/2026
BOS
Boston Airport
2h 12m
Non-stop
21:04
05/08/2026
ORD
Chicago Airport
₹9,479
per person
✕ Non-refundable14 fare options
JetBlue Airways
B6-311
07:02
05/08/2026
BOS
Boston Airport
1h 57m
Non-stop
08:59
05/08/2026
ORD
Chicago Airport
₹9,759
per person
✕ Non-refundable5 fare options
JetBlue Airways
B6-811
18:47
05/08/2026
BOS
Boston Airport
2h 6m
Non-stop
20:53
05/08/2026
ORD
Chicago Airport
₹9,759
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-2816
12:55
05/08/2026
BOS
Boston Airport
1h 53m
Non-stop
14:48
05/08/2026
ORD
Chicago Airport
₹9,956
per person
✕ Non-refundable3 fare options
Southwest Airlines
WN-898
15:45
05/08/2026
BOS
Boston Airport
1h 45m
Non-stop
17:30
05/08/2026
MDW
Chicago Airport
₹10,006
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-776
10:40
05/08/2026
BOS
Boston Airport
1h 40m
Non-stop
12:20
05/08/2026
MDW
Chicago Airport
₹10,137
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-961
07:10
05/08/2026
BOS
Boston Airport
1h 50m
Non-stop
09:00
05/08/2026
MDW
Chicago Airport
₹10,930
per person
✕ Non-refundable🔥 Last 1 seats6 fare options
Southwest Airlines
WN-888
17:50
05/08/2026
BOS
Boston Airport
6h 5m
1 Stop
⏱ DAL · 0h 45mDAL Airport
23:55
05/08/2026
MDW
Chicago Airport
₹11,072
per person
✕ Non-refundable
United Airlines
UA-1869
06:00
05/08/2026
BOS
Boston Airport
2h 0m
Non-stop
08:00
05/08/2026
ORD
Chicago Airport
₹11,670
per person
✕ Non-refundable7 fare options
United Airlines
UA-283
07:30
05/08/2026
BOS
Boston Airport
2h 0m
Non-stop
09:30
05/08/2026
ORD
Chicago Airport
₹11,670
per person
✕ Non-refundable7 fare options
United Airlines
UA-1170
08:05
05/08/2026
BOS
Boston Airport
2h 1m
Non-stop
10:06
05/08/2026
ORD
Chicago Airport
₹11,670
per person
✕ Non-refundable🔥 Last 3 seats7 fare options
Southwest Airlines
WN-3665
18:55
05/08/2026
BOS
Boston Airport
1h 50m
Non-stop
20:45
05/08/2026
MDW
Chicago Airport
₹11,855
per person
✕ Non-refundable🔥 Last 2 seats6 fare options
American Airlines
AA-2976
12:22
05/08/2026
BOS
Boston Airport
2h 3m
Non-stop
14:25
05/08/2026
ORD
Chicago Airport
₹11,887
per person
✕ Non-refundable9 fare options
American Airlines
AA-2114
08:03
05/08/2026
BOS
Boston Airport
2h 9m
Non-stop
10:12
05/08/2026
ORD
Chicago Airport
₹11,887
per person
✕ Non-refundable9 fare options
United Airlines
UA-1693
19:26
05/08/2026
BOS
Boston Airport
4h 11m
1 Stop
⏱ EWR · 0h 57mEWR Airport
23:37
05/08/2026
ORD
Chicago Airport
₹12,048
per person
✕ Non-refundable7 fare options
American Airlines
AA-4486
10:32
05/08/2026
BOS
Boston Airport
2h 8m
Non-stop
12:40
05/08/2026
ORD
Chicago Airport
₹13,645
per person
✕ Non-refundable9 fare options
😕 No flights match your filters.
Boston (BOS)
Chicago (ORD)
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Boston to Chicago — what to expect when booking
The BOS–ORD route is served by multiple carriers throughout the year.
Fares on this route can move quickly — a price available now may not be there 30 minutes later.
If your dates are flexible, try shifting your departure by a day or two using the date strip above.
Mid-week departures often show lower base fares compared to weekend starts on many routes.
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❓ Frequently asked questions — Boston to Chicago flights
Generally yes — fares on most routes are most competitive around 4–6 weeks before departure. Booking earlier usually means better availability and a lower base fare when your dates are fixed.
The straight-line distance between Boston,USA (BOS) and Chicago,USA (ORD) is approximately shown in the route details above. Actual flying distance may vary slightly depending on routing.
Non-stop availability on this route varies by airline schedule and season. Use the filters below to quickly check whether direct options are available on your selected date.
Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.