Find cheap airline tickets from Boston to Chicago by date

Departure: Return: Sorted by:

$284

outward: Jun 23, 2023
11:35p BOS » 11:15p ORD
Spirit Airlines 1 stop (23h40m)

inbound: Jun 27, 2023
12:10a ORD » 3:02p BOS
Unknown Company 1 stop (14h52m)

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$296

outward: Jun 16, 2023
11:35p BOS » 6:33p ORD
Spirit Airlines 1 stop (18h58m)

inbound: Jun 18, 2023
12:45p MDW » 7:08p BOS
Unknown Company 1 stop (6h23m)

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$312

outward: Oct 6, 2023
5:44p BOS » 7:15p MDW
Frontier Airlines 1 stop (25h31m)

inbound: Oct 10, 2023
4:18a ORD » 6:45a BOS
United Airlines direct (2h27m)

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$2,795

outward: May 25, 2024
2:50a BOS » 2:45a ORD
Unknown Company 4 stops (47h55m)

inbound: May 27, 2024
9:40p ORD » 11:30p BOS
Unknown Company 3 stops (25h50m)

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$3,036

outward: May 25, 2024
12:20a BOS » 3:00a ORD
Unknown Company 3 stops (26h40m)

inbound: May 28, 2024
2:10a ORD » 1:50a BOS
Unknown Company 4 stops (47h40m)

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$4,159

outward: May 25, 2024
3:15a BOS » 2:45a ORD
Unknown Company 4 stops (47h30m)

inbound: May 27, 2024
9:40p ORD » 11:50p BOS
Unknown Company 3 stops (26h10m)

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$4,556

outward: May 25, 2024
12:20a BOS » 3:00a ORD
Unknown Company 3 stops (26h40m)

inbound: May 27, 2024
10:45p ORD » 2:05a BOS
Unknown Company 3 stops (27h20m)

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Return

Departure

Choose when you'd like to depart to Chicago (USA):

Find the cheapest Boston Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Boston - Chicago with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Boston to Chicago

Departure: Airline

Spirit Airlines

outbound: Jun 16, 2023
Spirit Airlines 1 stop

return: Jun 18, 2023
Frontier Airlines 1 stop

$275 Verify

United Airlines

outbound: Oct 6, 2023
United Airlines direct

return: Oct 9, 2023
United Airlines direct

$433 Verify

American Airlines

outbound: Jun 23, 2023
American Airlines direct

return: Jun 26, 2023
Delta Air Lines 1 stop

$355 Verify

Airline tickets Boston - Chicago found in the last 30 days.

Travel tips for flights Boston - Chicago

Arrival city:
Chicago, USA
Airport(s):
Chicago Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
Jun 8, 2023 8:23 PM, GMT-5
Weather:
min. 58ºF, max. 78ºF

Departure city:
Boston, USA
Airport(s):
Boston Logan International Airport (BOS)
Manchester–Boston Regional Airport (MHT)
Local time:
Jun 8, 2023 9:23 PM, GMT-4
Weather:
min. 52ºF, max. 62ºF

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