Fares on this route currently start from ₹6,989. Compare live ORD to BOS prices, non-stop and connecting flights, departure times and airline choices before booking. Use the search panel to change origin, destination, passengers, cabin and trip type instantly.
ORD → BOS14 Jul 2026Live inventory
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Showing 25
of 123
live flights
Delta Air Lines
DL-2828
06:59
07/14/2026
ORD
Chicago Airport
3h 31m
Non-stop
10:30
07/14/2026
BOS
Boston Airport
₹6,989
per person
✕ Non-refundable7 fare options
Delta Air Lines
DL-2646
19:25
07/14/2026
ORD
Chicago Airport
3h 35m
Non-stop
23:00
07/14/2026
BOS
Boston Airport
₹6,989
per person
✕ Non-refundable7 fare options
Delta Air Lines
DL-2816
15:19
07/14/2026
ORD
Chicago Airport
3h 40m
Non-stop
18:59
07/14/2026
BOS
Boston Airport
₹6,989
per person
✕ Non-refundable7 fare options
Southwest Airlines
WN-1374
18:05
07/14/2026
MDW
Chicago Airport
3h 20m
Non-stop
21:25
07/14/2026
BOS
Boston Airport
₹7,320
per person
✕ Non-refundable10 fare options
American Airlines
AA-3022
06:00
07/14/2026
ORD
Chicago Airport
3h 34m
Non-stop
09:34
07/14/2026
BOS
Boston Airport
₹7,668
per person
✕ Non-refundable17 fare options
American Airlines
AA-2968
06:54
07/14/2026
ORD
Chicago Airport
3h 34m
Non-stop
10:28
07/14/2026
BOS
Boston Airport
₹7,668
per person
✕ Non-refundable17 fare options
American Airlines
AA-2682
20:29
07/14/2026
ORD
Chicago Airport
3h 36m
Non-stop
00:05
07/15/2026
+1
BOS
Boston Airport
₹7,668
per person
✕ Non-refundable16 fare options
American Airlines
AA-3107
19:29
07/14/2026
ORD
Chicago Airport
3h 37m
Non-stop
23:06
07/14/2026
BOS
Boston Airport
₹7,668
per person
✕ Non-refundable16 fare options
JetBlue Airways
B6-1206
06:00
07/14/2026
ORD
Chicago Airport
8h 48m
1 Stop
⏱ JFK · 4h 8mJFK Airport
14:48
07/14/2026
BOS
Boston Airport
₹8,796
per person
✕ Non-refundable5 fare options
JetBlue Airways
B6-1012
20:10
07/14/2026
ORD
Chicago Airport
3h 31m
Non-stop
23:41
07/14/2026
BOS
Boston Airport
₹9,053
per person
✕ Non-refundable5 fare options
JetBlue Airways
B6-312
10:56
07/14/2026
ORD
Chicago Airport
3h 27m
Non-stop
14:23
07/14/2026
BOS
Boston Airport
₹9,053
per person
✕ Non-refundable5 fare options
JetBlue Airways
B6-906
09:40
07/14/2026
ORD
Chicago Airport
7h 37m
1 Stop
⏱ JFK · 2h 51mJFK Airport
17:17
07/14/2026
BOS
Boston Airport
₹9,081
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-4975
14:40
07/14/2026
MDW
Chicago Airport
3h 20m
Non-stop
18:00
07/14/2026
BOS
Boston Airport
₹9,268
per person
✕ Non-refundable10 fare options
Southwest Airlines
WN-4611
07:40
07/14/2026
MDW
Chicago Airport
3h 15m
Non-stop
10:55
07/14/2026
BOS
Boston Airport
₹9,798
per person
✕ Non-refundable10 fare options
Southwest Airlines
WN-2641
12:45
07/14/2026
MDW
Chicago Airport
3h 20m
Non-stop
16:05
07/14/2026
BOS
Boston Airport
₹9,798
per person
✕ Non-refundable🔥 Last 5 seats10 fare options
Delta Air Lines
DL-2570
10:28
07/14/2026
ORD
Chicago Airport
3h 31m
Non-stop
13:59
07/14/2026
BOS
Boston Airport
₹10,238
per person
✕ Non-refundable7 fare options
JetBlue Airways
B6-906
09:40
07/14/2026
ORD
Chicago Airport
9h 19m
1 Stop
⏱ JFK · 4h 26mJFK Airport
18:59
07/14/2026
BOS
Boston Airport
₹10,286
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-1405
09:00
07/14/2026
MDW
Chicago Airport
3h 15m
Non-stop
12:15
07/14/2026
BOS
Boston Airport
₹10,415
per person
✕ Non-refundable10 fare options
United Airlines
UA-1186
06:05
07/14/2026
ORD
Chicago Airport
3h 24m
Non-stop
09:29
07/14/2026
BOS
Boston Airport
₹10,808
per person
✕ Non-refundable11 fare options
United Airlines
UA-1779
21:41
07/14/2026
ORD
Chicago Airport
3h 33m
Non-stop
01:14
07/15/2026
+1
BOS
Boston Airport
₹10,808
per person
✕ Non-refundable11 fare options
United Airlines
UA-2466
15:55
07/14/2026
ORD
Chicago Airport
3h 35m
Non-stop
19:30
07/14/2026
BOS
Boston Airport
₹10,808
per person
✕ Non-refundable11 fare options
United Airlines
UA-794
12:53
07/14/2026
ORD
Chicago Airport
3h 36m
Non-stop
16:29
07/14/2026
BOS
Boston Airport
₹10,808
per person
✕ Non-refundable🔥 Last 5 seats11 fare options
United Airlines
UA-1693
13:55
07/14/2026
ORD
Chicago Airport
3h 36m
Non-stop
17:31
07/14/2026
BOS
Boston Airport
₹10,808
per person
✕ Non-refundable🔥 Last 2 seats11 fare options
United Airlines
UA-2331
18:20
07/14/2026
ORD
Chicago Airport
3h 36m
Non-stop
21:56
07/14/2026
BOS
Boston Airport
₹10,808
per person
✕ Non-refundable11 fare options
United Airlines
UA-1032
19:45
07/14/2026
ORD
Chicago Airport
3h 36m
Non-stop
23:21
07/14/2026
BOS
Boston Airport
₹10,808
per person
✕ Non-refundable11 fare options
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Chicago (ORD)
Boston (BOS)
📅 Results on this page are loaded for 14 Jul 2026. Click Load more flights to expand the full list on this page.
Chicago to Boston — what to expect when booking
The ORD–BOS 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.
Before you book
Compare nearby dates
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❓ Frequently asked questions — Chicago to Boston 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 Chicago,USA (ORD) and Boston,USA (BOS) 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.