Cheap Flights from Boston to Chicago

Boston → Chicago
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🇺🇸 United States €42
🇹🇷 Turkey €260
🇪🇸 Spain €211
🇵🇹 Portugal €202
🇮🇹 Italy €239
🇫🇷 France €187
🇬🇧 United Kingdom €184
🇵🇷 Puerto Rico €125
← Back Home› Deals› Chicago (45)
Chicago — United States
Boston → Chicago
🇺🇸 United States · 45 flights from €61
7 Oct
13:23
UA · 2h 52m
✈ Direct
€61
6 Oct
00:31
UA · 2h 58m
✈ Direct
€61
10 Sep
10:55
B6 · 2h 51m
✈ Direct
€62
9 Oct
02:00
WN · 2h 35m
✈ Direct
€67
10 Sep
17:34
AA · 3h 1m
✈ Direct
€70
7 Sep
10:14
AA · 3h 6m
✈ Direct
€70
15 Sep
14:38
UA · 2h 51m
✈ Direct
€74
4 Sep
09:01
B6 · 4h 47m
€77
22 Sep
16:52
F9 · 6h 31m
€79
3 Sep
12:27
AA · 3h 3m
✈ Direct
€79
15 Sep
16:52
F9 · 6h 31m
€80
10 Sep
15:17
F9 · 12h 42m
€86
24 Sep
16:54
F9 · 11h 50m
€88
€87
17 Sep
10:55
B6 · 5h 52m
€87
4 Sep
16:45
F9 · 11h 2m
€87
16 Sep
11:00
B6 · 2h 48m
€89
1 Oct
10:55
B6 · 5h 52m
€91
23 Sep
14:38
UA · 2h 51m
✈ Direct
€91
3 Sep
09:01
B6 · 4h 44m
€92
7 Sep
09:01
B6 · 4h 47m
✈ Direct ↓30% 🔥
€93
HOT
1 Sep
16:57
B6 · 5h 38m
€93
6 Sep
20:30
B6 · 6h 25m
€93
29 Oct
10:00
UA · 3h
✈ Direct
€93
3 Sep
16:45
F9 · 11h 2m
€94
25 Sep
00:20
WN · 2h 40m
✈ Direct
€95
4 Oct
10:05
B6 · 30h 35m
€96
10 Oct
10:00
AA · 3h 2m
✈ Direct
€96
14 Oct
10:55
B6 · 2h 51m
✈ Direct
€97
19 Sep
12:40
WN · 2h 35m
✈ Direct
€98
16 Sep
14:05
WN · 2h 30m
✈ Direct
€98
26 Sep
11:05
WN · 2h 35m
✈ Direct
€99
19 Sep
17:34
AA · 3h 1m
✈ Direct
€99
7 Oct
10:55
B6 · 2h 54m
✈ Direct
€99
9 Sep
17:34
AA · 3h 1m
✈ Direct
€100
21 Sep
09:15
B6 · 5h 43m
€101
24 Sep
09:15
B6 · 5h 43m
€103
11 Oct
10:00
AA · 3h 2m
✈ Direct
€103
20 Sep
11:00
B6 · 2h 48m
✈ Direct
€105
22 Sep
00:20
WN · 2h 40m
✈ Direct
€106
25 Sep
18:45
B6 · 9h 23m
✈ Direct
€108
9 Nov
16:15
B6 · 3h 5m
✈ Direct
€111
27 Sep
11:00
B6 · 2h 48m
✈ Direct
€111
20 Sep
11:05
UA · 2h 58m
✈ Direct
€111
7 Sep
12:05
UA · 2h 59m
✈ Direct
€111
10 Oct
01:45
WN · 10h 45m
€124
With a stop
5 Sep
21:55
BOS → BWI → CHI
WN + F9 · 0d 21h stopover in Baltimore
€82
2 flights
☕ 21h in Baltimore — enough time to explore
9 Sep
09:25
BOS → BWI → CHI
WN + F9 · 1d 3h stopover in Baltimore
€109
2 flights
☕ 27h in Baltimore — enough time to explore
29 Sep
18:19
BOS → WAS → CHI
B6 + F9 · 2h layover in Washington
€121
2 flights
15 Sep
18:19
BOS → WAS → CHI
B6 + F9 · 2h layover in Washington
€128
2 flights
9 Sep
16:54
BOS → LAS → CHI
F9 + F9 · 1d 1h stopover in Las Vegas
€129
2 flights
☕ 25h in Las Vegas — enough time to explore
16 Sep
17:05
BOS → FLL → CHI
F9 + F9 · 0d 15h stopover in Fort Lauderdale
€130
2 flights
☕ 15h in Fort Lauderdale — enough time to explore
30 Sep
16:54
BOS → FLL → CHI
F9 + F9 · 0d 13h stopover in Fort Lauderdale
€133
2 flights
☕ 13h in Fort Lauderdale — enough time to explore
9 Sep
18:45
BOS → ORL → CHI
WN + F9 · 11h layover in ORL
€137
2 flights
☕ 11h in ORL — enough time to explore

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€110€96
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