Cheap Flights from Chicago, IL to Boston, MA from $52

Return flight: Boston – Chicago

On Cheapflightsplus.com you will find 17 direct and 423 connecting flights from Chicago to Boston. You can compare airfare deals from 10 airlines and multiple travel sites from $52, book and save on cheap plane tickets and last minute offers. Also check out CHI-BOS flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Chicago to Boston Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $52 (one-way), $89 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from Chicago to Boston. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
06:30 — 09:56
06:30 — 09:56 UA2104 United Airlines
Chicago — Boston
2h 26m
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from$78
07:27 — 10:54
07:27 — 10:54 UA2067 United Airlines
Chicago — Boston
2h 27m
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from$78
09:07 — 12:42
09:07 — 12:42 UA1346 United Airlines
Chicago — Boston
2h 35m
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from$81
09:13 — 12:48
09:13 — 12:48 UA536 United Airlines
Chicago — Boston
2h 35m
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from$78
09:20 — 12:48
09:20 — 12:48 UA721 United Airlines
Chicago — Boston
2h 28m
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from$181
13:12 — 16:43
13:12 — 16:43 UA2022 United Airlines
Chicago — Boston
2h 31m
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from$123
13:30 — 17:02
13:30 — 17:02 UA1262 United Airlines
Chicago — Boston
2h 32m
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from$81
14:15 — 17:46
14:15 — 17:46 UA1693 United Airlines
Chicago — Boston
2h 31m
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from$81
14:15 — 17:46
14:15 — 17:46 UA664 United Airlines
Chicago — Boston
2h 31m
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from$123
14:28 — 18:06
14:28 — 18:06 UA2138 United Airlines
Chicago — Boston
2h 38m
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from$78
14:28 — 18:06
14:28 — 18:06 UA2370 United Airlines
Chicago — Boston
2h 38m
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from$78
16:20 — 19:48
16:20 — 19:48 UA1677 United Airlines
Chicago — Boston
2h 28m
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from$181
17:57 — 21:28
17:57 — 21:28 UA1531 United Airlines
Chicago — Boston
2h 31m
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from$102
18:04 — 21:35
18:04 — 21:35 UA1989 United Airlines
Chicago — Boston
2h 31m
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from$81
19:45 — 23:12
19:45 — 23:12 UA1129 United Airlines
Chicago — Boston
2h 27m
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from$78
19:53 — 23:20
19:53 — 23:20 UA2444 United Airlines
Chicago — Boston
2h 27m
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from$78
21:32 — 00:59
+1 day
21:32 — 00:59 UA1779 United Airlines
Chicago — Boston
2h 27m
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from$78
05:05 — 14:44
05:05 — 09:06 NK2 Spirit Airlines
Chicago — Miami
2h 23m stop
12:29 — 15:44 NK2126 Spirit Airlines
Miami — Boston
8h 39m
including layover
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from$54
05:05 — 19:34
05:05 — 09:12 NK1 Spirit Airlines
Chicago — Miami
7h 3m stop
16:15 — 19:34 NK1230 Spirit Airlines
Miami — Boston
13h 29m
including layover
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from$81
06:00 — 13:40
06:00 — 09:10 UA1658 United Airlines
Chicago — Newark
3h 12m stop
15:04 — 16:19 UA593 United Airlines
Newark — Boston
6h 40m
including layover
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from$98
07:15 — 15:35
07:15 — 11:03 NK3200 Spirit Airlines
Chicago — Orlando
1h 27m stop
12:30 — 15:35 NK3796 Spirit Airlines
Orlando — Boston
7h 20m
including layover
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from$52
08:35 — 08:35
+1 day
08:35 — 12:20 F91458 Frontier Airlines
Chicago — Orlando
17h 10m stop
05:30 — 08:35 F93348 Frontier Airlines
Orlando — Boston
23h
including layover
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from$71
08:47 — 15:32
08:45 — 12:09 UA2691 United Airlines
Chicago — Newark
2h 5m stop
15:00 — 16:19 UA577 United Airlines
Newark — Boston
5h 45m
including layover
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from$98
10:00 — 16:24
10:00 — 13:06 NK2708 Spirit Airlines
Chicago — Atlanta
48m stop
13:54 — 16:24 NK2092 Spirit Airlines
Atlanta — Boston
5h 24m
including layover
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from$75
10:33 — 22:51
10:33 — 13:19 NK2440 Spirit Airlines
Chicago — Baltimore
8h 5m stop
21:24 — 22:51 NK2105 Spirit Airlines
Baltimore — Boston
11h 18m
including layover
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from$75
11:11 — 21:54
11:11 — 14:11 NK1819 Spirit Airlines
Chicago — Myrtle Beach
5h 35m stop
19:46 — 21:54 NK1005 Spirit Airlines
Myrtle Beach — Boston
9h 43m
including layover
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from$66
11:21 — 19:21
11:21 — 13:51 NK1633 Spirit Airlines
Chicago — Dallas
45m stop
14:36 — 19:21 NK1838 Spirit Airlines
Dallas — Boston
7h
including layover
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from$66
12:41 — 23:29
12:41 — 16:44 NK2187 Spirit Airlines
Chicago — Miami
3h 29m stop
20:13 — 23:29 NK2212 Spirit Airlines
Miami — Boston
9h 48m
including layover
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from$81
13:11 — 09:11
+1 day
13:11 — 15:49 G41846 Allegiant Air
Chicago — Fletcher
15h 11m stop
07:00 — 09:11 G4228 Allegiant Air
Fletcher — Boston
19h
including layover
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from$79
15:29 — 00:39
+1 day
15:29 — 19:39 NK867 Spirit Airlines
Chicago — Miami
1h 46m stop
21:25 — 00:39 NK616 Spirit Airlines
Miami — Boston
8h 10m
including layover
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from$52
16:06 — 00:43
+1 day
16:00 — 19:43 F91186 Frontier Airlines
Chicago — Tampa
1h 35m stop
06:20 — 09:34 F91216 Frontier Airlines
Tampa — Boston
7h 37m
including layover
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from$85
16:37 — 08:35
+1 day
09:58 — 13:42 F92792 Frontier Airlines
Chicago — Orlando
8h 51m stop
05:30 — 08:40 F93348 Frontier Airlines
Orlando — Boston
14h 58m
including layover
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from$71
20:36 — 09:12
+1 day
20:36 — 23:13 G4248 Allegiant Air
Chicago — Fletcher
7h 47m stop
07:00 — 09:12 G4228 Allegiant Air
Fletcher — Boston
11h 36m
including layover
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from$79
12:41 — 15:56
+1 day
12:41 — 16:44 NK2187 Spirit Airlines
Chicago — Miami
3h 21m stop
20:05 — 22:41 NK2156 Spirit Airlines
Miami — Baltimore
15h 49m stop
14:30 — 15:56 NK2105 Spirit Airlines
Baltimore — Boston
26h 15m
including layover
Find flight
from$96
17:10 — 15:35
+1 day
17:10 — 20:28 NK328 Spirit Airlines
Chicago — Newark
9h 17m stop
05:45 — 08:34 NK1801 Spirit Airlines
Newark — Orlando
3h 56m stop
12:30 — 15:35 NK3796 Spirit Airlines
Orlando — Boston
21h 25m
including layover
Find flight
from$87
17:10 — 18:18
+1 day
17:10 — 20:28 NK328 Spirit Airlines
Chicago — Newark
16h 50m stop
13:18 — 15:13 NK3021 Spirit Airlines
Newark — Myrtle Beach
55m stop
16:08 — 18:18 NK138 Spirit Airlines
Myrtle Beach — Boston
24h 8m
including layover
Find flight
from$87
20:12 — 15:35
+1 day
20:12 — 23:31 NK919 Spirit Airlines
Chicago — Newark
6h 14m stop
05:45 — 08:34 NK1801 Spirit Airlines
Newark — Orlando
3h 56m stop
12:30 — 15:35 NK3796 Spirit Airlines
Orlando — Boston
18h 23m
including layover
Find flight
from$90
21:08 — 09:09
+2 days
21:08 — 00:29 NK2542 Spirit Airlines
Chicago — Newark
21h 26m stop
21:55 — 00:45 NK2116 Spirit Airlines
Newark — Orlando
5h 22m stop
06:07 — 09:09 NK2090 Spirit Airlines
Orlando — Boston
35h 1m
including layover
Find flight
from$75
*Departure and arrival times - local. Updated on June 2, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Chicago to Boston depends on and how to choose the most interesting flight option for you.

Distance between Chicago and Boston is 1370 miles. Time difference between the cities is 1h. Airplanes depart 05:05 to 22:15 from 7 Chicago airports and arrive 05:05 to 22:15 to 4 Boston airports. Average flight time is 2h 31m.

  • The fastest flight 2h 26m
  • Average flight time 2h 31m
  • The earliest flight 05:05
  • The latest flight 22:15
  • Distance 852 ml

The cheapest months to travel to Boston are october (from 70 $), june (from 72 $), may (from 81 $).

The most expensive months are november (from 258 $), september (from 97 $), july (from 89 $).

What is the lowest airfare Chicago to Boston?

The cheapest plane ticket found by our users is $52. This airfare is for economy class on one-way NK867 flight by Spirit Airlines for October 7, 2025 which leaves O'Hare International in Chicago at 15:29 am and arrives at Boston Logan at 00:39.

Economy class
$52
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Business class
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First class
?
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Popular Airlines on the Route

The flight Chicago — Boston is served by 10 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by United Airlines - 193 departures per week at the price of from $ 78 . And the most expensive tickets are offered by Finnair airline - from $ 2644.

Direct flights

There are 17 nonstop flights on the route. The fastest direct flight is UA2104 by United Airlines takes 2h 26m and the cheapest is NK867 by Spirit Airlines for $78.

See more direct flights

Connecting Flights

There are 423 flights with layovers on the route. The fastest connecting flight is UA1068 by United Airlines takes 4h 20m and the cheapest is NK867 by Spirit Airlines for $52.

  • from $87
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  • from $52
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  • AS - Alaska Airlines
    from $156
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  • F9 - Frontier Airlines
    from $71
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  • SY - Sun Country Airlines
    from $101
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  • TK - Turkish Airlines
    from $1988
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  • AY - Finnair
    from $786
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  • HA - Hawaiian Airlines
    from $182
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  • LF - flynordic
    from $138
    Find
  • G4 - Allegiant Air
    from $79
    Find
See more connecting flights

Airports

You can fly from Chicago to Boston from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

  • O'Hare International-ORD
    from $52
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  • Midway-MDW
    from $71
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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Boston airports

  • Boston City Heliport-JBC
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  • Boston RT128 Rail-ZRU
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  • Boston South Rail-ZTO
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  • Logan-BOS
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How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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