Cheap flights from Chicago to Boston from $0
Compare prices across airlines and find the best deals
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Discover deals on Chicago to Boston flights
Typical range $0–$0•Cheapest found $0
Checking latest prices...Find cheap flights from Chicago to Boston
Best
9 Feb
DEP
16:30
ORD
19:44
BOS
2h 14m
9 Feb
DEPARTURE
16:30 - 19:44
2h 14m
ORD
BOS
9 Feb
DEP
17:25
ORD
20:45
BOS
2h 20m
9 Feb
DEPARTURE
17:25 - 20:45
2h 20m
ORD
BOS
American Airlines flights from Chicago to Boston
Our best American Airlines deals on Chicago to Boston tickets
Best
9 Feb
DEP
16:30
ORD
19:44
BOS
2h 14m
9 Feb
DEPARTURE
16:30 - 19:44
2h 14m
ORD
BOS
9 Feb
DEP
17:25
ORD
20:45
BOS
2h 20m
9 Feb
DEPARTURE
17:25 - 20:45
2h 20m
ORD
BOS
Spirit Airlines flights from Chicago to Boston
Our best Spirit Airlines deals on Chicago to Boston tickets
Best
1 stop
9 Feb
DEP
12:44
ORD
1×
23:19
BOS
9h 35m
9 Feb
DEPARTURE
12:44 - 23:19
9h 35m
ORD
1 stop
BOS
1 stop
9 Feb
DEP
10:48
ORD
1×
23:19
BOS
11h 31m
9 Feb
DEPARTURE
10:48 - 23:19
11h 31m
ORD
1 stop
BOS
What's the cheapest day of the week to fly from Chicago to Boston?
If your flying dates are flexible, you should consider flying to Boston on a Thu, as we generally find the cheapest rates on that day. On the other hand, Sat is the most expensive day to fly.
What is the cheapest month to fly from Chicago to Boston?
The cheapest month for flights from Chicago to Boston is Sep, where tickets cost $93 on average. The most expensive months are Jul.
JanFebMarAprMayJunJulAugSepOctNovDec
$134$114$93
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Everything you should know
Cheapest one-way flight
$99
Typical prices: $99–$399
When to book
6 weeks
in advance to save around 35%
Good to know
💰
Save money
Compare prices across airlines to find the best deal. Prices can vary significantly.
📅
Be flexible
Flying midweek or in off-peak seasons can save you up to 30% on airfare.
⏰
Book early
Booking 6+ weeks in advance typically offers the best prices.
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Frequently asked questions
The cheapest flight from Chicago to Boston currently costs AUD $99. Prices typically range from $99 to $399. Prices change frequently, so we recommend booking early and being flexible with your travel dates.