Cheap Flights from Boston, MA to Chicago, IL from $98

Return flight: Chicago – Boston

On Cheapflightsplus.com you will find 3 direct and 50 connecting flights from Boston to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $98, book and save on cheap plane tickets and last minute offers. Also check out BOS-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Boston to Chicago 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: $98 (one-way), $168 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from Boston to Chicago. 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
07:45 — 09:41
07:45 — 09:41 UA2251 United Airlines
Boston — Chicago
2h 56m
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from$107
09:43 — 11:33
09:43 — 11:33 UA365 United Airlines
Boston — Chicago
2h 50m
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from$107
12:30 — 14:20
12:30 — 14:20 UA1732 United Airlines
Boston — Chicago
2h 50m
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from$107
05:30 — 09:36
05:30 — 07:10 UA1734 United Airlines
Boston — Washington D.C.
1h 10m stop
08:20 — 09:36 UA2401 United Airlines
Washington D.C. — Chicago
5h 6m
including layover
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from$142
05:30 — 17:10
05:30 — 07:10 UA1734 United Airlines
Boston — Washington D.C.
8h 45m stop
15:55 — 17:10 UA265 United Airlines
Washington D.C. — Chicago
12h 40m
including layover
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from$247
06:05 — 19:07
06:05 — 09:33 NK2448 Spirit Airlines
Boston — Miami
7h 16m stop
16:49 — 19:07 NK2125 Spirit Airlines
Miami — Chicago
14h 2m
including layover
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from$98
06:05 — 23:59
06:05 — 09:33 NK2448 Spirit Airlines
Boston — Miami
12h 14m stop
21:47 — 23:59 NK2 Spirit Airlines
Miami — Chicago
18h 54m
including layover
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from$133
07:10 — 17:00
07:10 — 08:35 UA570 United Airlines
Boston — Newark
6h 50m stop
15:25 — 17:00 UA2394 United Airlines
Newark — Chicago
10h 50m
including layover
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from$260
08:05 — 18:29
08:05 — 09:30 UA309 United Airlines
Boston — Newark
7h 19m stop
16:49 — 18:29 UA661 United Airlines
Newark — Chicago
11h 24m
including layover
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from$260
09:30 — 14:29
09:30 — 11:13 UA2098 United Airlines
Boston — Washington D.C.
2h 2m stop
13:15 — 14:29 UA2331 United Airlines
Washington D.C. — Chicago
5h 59m
including layover
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from$149
10:34 — 22:22
10:34 — 13:47 NK426 Spirit Airlines
Boston — Orlando
6h 36m stop
20:23 — 22:22 NK2343 Spirit Airlines
Orlando — Chicago
12h 48m
including layover
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from$98
12:25 — 15:43
+1 day
12:25 — 14:34 NK2301 Spirit Airlines
Boston — Myrtle Beach
23h 44m stop
14:18 — 15:43 NK2074 Spirit Airlines
Myrtle Beach — Chicago
28h 18m
including layover
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from$111
13:00 — 17:10
13:00 — 14:43 UA2692 United Airlines
Boston — Washington D.C.
1h 12m stop
15:55 — 17:10 UA265 United Airlines
Washington D.C. — Chicago
5h 10m
including layover
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from$141
13:00 — 19:48
13:00 — 14:43 UA2692 United Airlines
Boston — Washington D.C.
3h 57m stop
18:40 — 19:48 UA2304 United Airlines
Washington D.C. — Chicago
7h 48m
including layover
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from$141
14:53 — 22:22
14:53 — 18:11 NK2179 Spirit Airlines
Boston — Orlando
2h 12m stop
20:23 — 22:22 NK2343 Spirit Airlines
Orlando — Chicago
8h 29m
including layover
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from$98
14:53 — 16:10
+1 day
14:53 — 18:11 NK2179 Spirit Airlines
Boston — Orlando
19h 56m stop
14:07 — 16:10 NK2410 Spirit Airlines
Orlando — Chicago
26h 17m
including layover
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from$133
15:25 — 09:22
+1 day
15:25 — 19:06 NK2839 Spirit Airlines
Boston — Miami
11h 54m stop
07:00 — 09:22 NK2530 Spirit Airlines
Miami — Chicago
18h 57m
including layover
Find flight
from$133
16:12 — 15:43
+1 day
16:12 — 18:29 NK2512 Spirit Airlines
Boston — Myrtle Beach
19h 49m stop
14:18 — 15:43 NK2074 Spirit Airlines
Myrtle Beach — Chicago
24h 31m
including layover
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from$111
16:38 — 16:10
+1 day
16:38 — 19:57 NK2723 Spirit Airlines
Boston — Orlando
18h 10m stop
14:07 — 16:10 NK2410 Spirit Airlines
Orlando — Chicago
24h 32m
including layover
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from$133
18:55 — 19:07
+1 day
18:55 — 22:18 NK2303 Spirit Airlines
Boston — Miami
18h 31m stop
16:49 — 19:07 NK2125 Spirit Airlines
Miami — Chicago
25h 12m
including layover
Find flight
from$144
18:55 — 23:59
+1 day
18:55 — 22:18 NK2303 Spirit Airlines
Boston — Miami
23h 29m stop
21:47 — 23:59 NK2 Spirit Airlines
Miami — Chicago
30h 4m
including layover
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from$144
19:05 — 23:25
19:05 — 20:45 UA3571 United Airlines
Boston — Newark
59m stop
21:44 — 23:25 UA1308 United Airlines
Newark — Chicago
5h 20m
including layover
Find flight
from$214
19:12 — 23:15
19:00 — 20:46 UA2136 United Airlines
Boston — Washington D.C.
1h 15m stop
22:18 — 23:30 UA1738 United Airlines
Washington D.C. — Chicago
5h 3m
including layover
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from$142
20:23 — 13:01
+1 day
20:23 — 23:52 AS249 Alaska Airlines
Boston — San Francisco
6h 38m stop
06:30 — 13:01 UA587 United Airlines
San Francisco — Chicago
17h 38m
including layover
Find flight
from$727
10:34 — 11:10
+1 day
10:34 — 13:47 NK426 Spirit Airlines
Boston — Orlando
4h 53m stop
18:40 — 21:02 NK2022 Spirit Airlines
Orlando — Baltimore
13h 2m stop
10:04 — 11:10 NK2072 Spirit Airlines
Baltimore — Chicago
25h 36m
including layover
Find flight
from$141
15:25 — 11:10
+1 day
15:25 — 19:06 NK2839 Spirit Airlines
Boston — Miami
2h 23m stop
21:29 — 23:59 NK2737 Spirit Airlines
Miami — Baltimore
10h 5m stop
10:04 — 11:10 NK2072 Spirit Airlines
Baltimore — Chicago
20h 45m
including layover
Find flight
from$164
*Departure and arrival times - local. Updated on July 24, 2025

Flight Information

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

Distance between Boston and Chicago is 1370 miles. Time difference between the cities is 1h. Airplanes depart 05:30 to 20:23 from 4 Boston airports and arrive 05:30 to 20:23 to 7 Chicago airports. Average flight time is 2h 50m.

  • The fastest flight 2h 50m
  • Average flight time 2h 50m
  • The earliest flight 05:30
  • The latest flight 20:23
  • Distance 852 ml

The cheapest months to travel to Chicago are august (from 98 $), october (from 110 $), september (from 113 $).

The most expensive months are november (from 143 $), june (from 138 $), may (from 138 $).

What is the lowest airfare Boston to Chicago?

The cheapest plane ticket found by our users is $98. This airfare is for economy class on one-way NK2448 flight by Spirit Airlines for August 30, 2025 which leaves Logan in Boston at 06:05 am and arrives at Chicago O'Hare International at 19:07.

Economy class
$98
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Business class
?
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First class
?
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Popular Airlines on the Route

The flight Boston — Chicago is served by 4 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by United Airlines - 21 departures per week at the price of from $ 107 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 727.

Direct flights

There are 3 nonstop flights on the route. The fastest direct flight is UA365 by United Airlines takes 2h 50m and the cheapest is NK2448 by Spirit Airlines for $107.

See more direct flights

Connecting Flights

There are 50 flights with layovers on the route. The fastest connecting flight is UA721 by United Airlines takes 4h 45m and the cheapest is NK2448 by Spirit Airlines for $98.

  • from $141
    Find
  • AS - Alaska Airlines
    from $727
    Find
  • HA - Hawaiian Airlines
    from $228
    Find
  • NK - Spirit Airlines
    from $98
    Find
See more connecting flights

Airports

You can fly from Boston to Chicago from 4 airports (Boston City Heliport, Boston RT128 Rail, Boston South Rail, Logan).

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
    from $98
    Find

Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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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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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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