Fares on this route currently start from ₹9,210. Compare live BOS to ORD 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.
BOS → ORD04 Jun 2026Live inventory
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Showing 25
of 132
live flights
Delta Air Lines
DL-2570
07:35
06/04/2026
BOS
Boston Airport
1h 52m
Non-stop
09:27
06/04/2026
ORD
Chicago Airport
₹9,210
per person
✕ Non-refundable7 fare options
Delta Air Lines
DL-2804
20:40
06/04/2026
BOS
Boston Airport
1h 55m
Non-stop
22:35
06/04/2026
ORD
Chicago Airport
₹9,210
per person
✕ Non-refundable7 fare options
Delta Air Lines
DL-2646
16:15
06/04/2026
BOS
Boston Airport
2h 0m
Non-stop
18:15
06/04/2026
ORD
Chicago Airport
₹9,210
per person
✕ Non-refundable7 fare options
American Airlines
AA-3324
05:01
06/04/2026
BOS
Boston Airport
1h 58m
Non-stop
06:59
06/04/2026
ORD
Chicago Airport
₹9,353
per person
✕ Non-refundable27 fare options
American Airlines
AA-1509
07:00
06/04/2026
BOS
Boston Airport
2h 3m
Non-stop
09:03
06/04/2026
ORD
Chicago Airport
₹9,353
per person
✓ Refundable27 fare options
American Airlines
AA-1554
19:46
06/04/2026
BOS
Boston Airport
2h 14m
Non-stop
22:00
06/04/2026
ORD
Chicago Airport
₹9,353
per person
✓ Refundable21 fare options
Southwest Airlines
WN-3239
05:25
06/04/2026
BOS
Boston Airport
1h 35m
Non-stop
07:00
06/04/2026
MDW
Chicago Airport
₹9,426
per person
✕ Non-refundable9 fare options
American Airlines
AA-3022
10:29
06/04/2026
BOS
Boston Airport
2h 1m
Non-stop
12:30
06/04/2026
ORD
Chicago Airport
₹9,731
per person
✓ Refundable21 fare options
United Airlines
UA-1414
06:00
06/04/2026
BOS
Boston Airport
1h 58m
Non-stop
07:58
06/04/2026
ORD
Chicago Airport
₹9,999
per person
✕ Non-refundable11 fare options
United Airlines
UA-366
07:19
06/04/2026
BOS
Boston Airport
1h 58m
Non-stop
09:17
06/04/2026
ORD
Chicago Airport
₹9,999
per person
✕ Non-refundable11 fare options
JetBlue Airways
B6-311
06:00
06/04/2026
BOS
Boston Airport
2h 0m
Non-stop
08:00
06/04/2026
ORD
Chicago Airport
₹10,006
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-745
07:30
06/04/2026
BOS
Boston Airport
1h 40m
Non-stop
09:10
06/04/2026
MDW
Chicago Airport
₹11,291
per person
✕ Non-refundable9 fare options
Frontier Airlines
F9-3085
06:00
06/04/2026
BOS
Boston Airport
5h 12m
1 Stop
⏱ ATL · 1h 0mATL Airport
11:12
06/04/2026
MDW
Chicago Airport
₹11,434
per person
✕ Non-refundable
American Airlines
AA-3711
13:56
06/04/2026
BOS
Boston Airport
2h 2m
Non-stop
15:58
06/04/2026
ORD
Chicago Airport
₹11,725
per person
✓ Refundable27 fare options
American Airlines
AA-1239
08:57
06/04/2026
BOS
Boston Airport
2h 3m
Non-stop
11:00
06/04/2026
ORD
Chicago Airport
₹11,725
per person
✓ Refundable27 fare options
American Airlines
AA-1610
12:01
06/04/2026
BOS
Boston Airport
2h 3m
Non-stop
14:04
06/04/2026
ORD
Chicago Airport
₹11,725
per person
✓ Refundable27 fare options
American Airlines
AA-872
15:10
06/04/2026
BOS
Boston Airport
2h 10m
Non-stop
17:20
06/04/2026
ORD
Chicago Airport
₹11,725
per person
✓ Refundable27 fare options
United Airlines
UA-503
10:35
06/04/2026
BOS
Boston Airport
1h 53m
Non-stop
12:28
06/04/2026
ORD
Chicago Airport
₹12,108
per person
✕ Non-refundable11 fare options
United Airlines
UA-1732
12:30
06/04/2026
BOS
Boston Airport
1h 53m
Non-stop
14:23
06/04/2026
ORD
Chicago Airport
₹12,108
per person
✕ Non-refundable11 fare options
American Airlines
AA-4435
07:05
06/04/2026
BOS
Boston Airport
3h 55m
1 Stop
⏱ IND · 0h 47mIND Airport
11:00
06/04/2026
ORD
Chicago Airport
₹12,656
per person
✕ Non-refundable26 fare options
American Airlines
AA-4386
13:13
06/04/2026
BOS
Boston Airport
2h 9m
Non-stop
15:22
06/04/2026
ORD
Chicago Airport
₹13,623
per person
✓ Refundable27 fare options
Frontier Airlines
F9-3511
09:12
06/04/2026
BOS
Boston Airport
10h 17m
1 Stop
⏱ ATL · 5h 49mATL Airport
19:29
06/04/2026
ORD
Chicago Airport
₹13,888
per person
✕ Non-refundable
Southwest Airlines
WN-3911
18:45
06/04/2026
BOS
Boston Airport
1h 50m
Non-stop
20:35
06/04/2026
MDW
Chicago Airport
₹14,535
per person
✕ Non-refundable9 fare options
United Airlines
UA-1349
09:50
06/04/2026
BOS
Boston Airport
1h 53m
Non-stop
11:43
06/04/2026
ORD
Chicago Airport
₹14,835
per person
✕ Non-refundable🔥 Last 1 seats11 fare options
United Airlines
UA-1834
08:15
06/04/2026
BOS
Boston Airport
1h 57m
Non-stop
10:12
06/04/2026
ORD
Chicago Airport
₹14,835
per person
✕ Non-refundable🔥 Last 2 seats11 fare options
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Boston (BOS)
Chicago (ORD)
📅 Results on this page are loaded for 04 Jun 2026. Click View all flights for the complete live search.
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.