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ORD → BOS11 May 2026Live inventory
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Showing 25
of 127
live flights
Delta Air Lines
DL-2828
07:00
05/11/2026
ORD
Chicago Airport
3h 35m
Non-stop
10:35
05/11/2026
BOS
Boston Airport
₹8,143
per person
✕ Non-refundable4 fare options
American Airlines
AA-2784
20:56
05/11/2026
ORD
Chicago Airport
3h 29m
Non-stop
00:25
05/12/2026
+1
BOS
Boston Airport
₹8,293
per person
✓ Refundable27 fare options
JetBlue Airways
B6-1012
07:20
05/11/2026
ORD
Chicago Airport
3h 26m
Non-stop
10:46
05/11/2026
BOS
Boston Airport
₹8,553
per person
✕ Non-refundable5 fare options
American Airlines
AA-3107
19:00
05/11/2026
ORD
Chicago Airport
3h 28m
Non-stop
22:28
05/11/2026
BOS
Boston Airport
₹9,604
per person
✓ Refundable25 fare options
American Airlines
AA-3209
10:55
05/11/2026
ORD
Chicago Airport
3h 31m
Non-stop
14:26
05/11/2026
BOS
Boston Airport
₹9,604
per person
✓ Refundable25 fare options
American Airlines
AA-2278
15:15
05/11/2026
ORD
Chicago Airport
3h 34m
Non-stop
18:49
05/11/2026
BOS
Boston Airport
₹9,604
per person
✓ Refundable25 fare options
Delta Air Lines
DL-2560
10:30
05/11/2026
ORD
Chicago Airport
3h 27m
Non-stop
13:57
05/11/2026
BOS
Boston Airport
₹10,056
per person
✕ Non-refundable4 fare options
Delta Air Lines
DL-2646
19:16
05/11/2026
ORD
Chicago Airport
3h 34m
Non-stop
22:50
05/11/2026
BOS
Boston Airport
₹10,056
per person
✕ Non-refundable4 fare options
Delta Air Lines
DL-2816
15:50
05/11/2026
ORD
Chicago Airport
3h 37m
Non-stop
19:27
05/11/2026
BOS
Boston Airport
₹10,056
per person
✕ Non-refundable4 fare options
United Airlines
UA-2213
06:00
05/11/2026
ORD
Chicago Airport
3h 25m
Non-stop
09:25
05/11/2026
BOS
Boston Airport
₹11,072
per person
✕ Non-refundable10 fare options
United Airlines
UA-1278
20:00
05/11/2026
ORD
Chicago Airport
3h 35m
Non-stop
23:35
05/11/2026
BOS
Boston Airport
₹11,072
per person
✕ Non-refundable10 fare options
Southwest Airlines
WN-3737
07:40
05/11/2026
MDW
Chicago Airport
3h 15m
Non-stop
10:55
05/11/2026
BOS
Boston Airport
₹11,939
per person
✕ Non-refundable🔥 Last 5 seats10 fare options
American Airlines
AA-4616
07:05
05/11/2026
ORD
Chicago Airport
3h 34m
Non-stop
10:39
05/11/2026
BOS
Boston Airport
₹12,040
per person
✕ Non-refundable18 fare options
American Airlines
AA-3325
08:05
05/11/2026
ORD
Chicago Airport
3h 27m
Non-stop
11:32
05/11/2026
BOS
Boston Airport
₹12,040
per person
✓ Refundable25 fare options
American Airlines
AA-2952
11:45
05/11/2026
ORD
Chicago Airport
3h 33m
Non-stop
15:18
05/11/2026
BOS
Boston Airport
₹12,040
per person
✓ Refundable24 fare options
American Airlines
AA-2837
17:39
05/11/2026
ORD
Chicago Airport
3h 33m
Non-stop
21:12
05/11/2026
BOS
Boston Airport
₹12,040
per person
✓ Refundable23 fare options
American Airlines
AA-2815
13:11
05/11/2026
ORD
Chicago Airport
3h 34m
Non-stop
16:45
05/11/2026
BOS
Boston Airport
₹12,040
per person
✓ Refundable18 fare options
United Airlines
UA-2437
16:25
05/11/2026
ORD
Chicago Airport
7h 34m
1 Stop
⏱ IAD · 2h 47mIAD Airport
23:59
05/11/2026
BOS
Boston Airport
₹12,961
per person
✕ Non-refundable🔥 Last 2 seats9 fare options
Delta Air Lines
DL-4678
18:36
05/11/2026
MDW
Chicago Airport
4h 53m
1 Stop
⏱ DTW · 0h 45mDTW Airport
23:29
05/11/2026
BOS
Boston Airport
₹14,654
per person
✕ Non-refundable
Delta Air Lines
DL-2358
17:19
05/11/2026
ORD
Chicago Airport
6h 10m
1 Stop
⏱ DTW · 1h 46mDTW Airport
23:29
05/11/2026
BOS
Boston Airport
₹14,801
per person
✕ Non-refundable3 fare options
Delta Air Lines
DL-1471
17:41
05/11/2026
ORD
Chicago Airport
6h 13m
1 Stop
⏱ MSP · 0h 44mMSP Airport
23:54
05/11/2026
BOS
Boston Airport
₹14,801
per person
✕ Non-refundable2 fare options
Delta Air Lines
DL-2239
14:45
05/11/2026
ORD
Chicago Airport
7h 40m
1 Stop
⏱ LGA · 3h 0mLGA Airport
22:25
05/11/2026
BOS
Boston Airport
₹14,801
per person
✕ Non-refundable3 fare options
Delta Air Lines
DL-2271
09:44
05/11/2026
ORD
Chicago Airport
8h 44m
1 Stop
⏱ LGA · 4h 0mLGA Airport
18:28
05/11/2026
BOS
Boston Airport
₹14,801
per person
✕ Non-refundable2 fare options
United Airlines
UA-1976
07:30
05/11/2026
ORD
Chicago Airport
3h 31m
Non-stop
11:01
05/11/2026
BOS
Boston Airport
₹14,856
per person
✕ Non-refundable10 fare options
United Airlines
UA-2060
15:55
05/11/2026
ORD
Chicago Airport
3h 31m
Non-stop
19:26
05/11/2026
BOS
Boston Airport
₹14,856
per person
✕ Non-refundable10 fare options
😕 No flights match your filters.
Chicago (ORD)
Boston (BOS)
📅 Results on this page are loaded for 11 May 2026. Click View all flights for the complete live search.
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.