Cheap Flights from Chicago, IL to Boston, MA from $101

Return flight: Boston – Chicago
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On Cheapflightsplus.com you will find 8 direct and 63 connecting flights from Chicago to Boston. You can compare airfare deals from 6 airlines and multiple travel sites from $101, 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: $101 (one-way), $173 (round-trip).
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Best Flights from Chicago to Boston Today

Take a look at the list of non stop flights and flights with layovers from Chicago to Boston with the lowest price of $101. The fastest direct flight takes 2h 26m and the fastest connecting – 4h 23m.
Price Departure Arrival Flight Duration Airline Flight
from $101
Find flight
09:13
Chicago
O'Hare International
 12:48
Boston
Logan
 2h 35m United Airlines
UA536
from $130
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17:57
Chicago
O'Hare International
 21:28
Boston
Logan
 2h 31m United Airlines
UA1531
from $158
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13:12
Chicago
O'Hare International
 16:43
Boston
Logan
 2h 31m United Airlines
UA2022
from $134
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07:15
Chicago
O'Hare International
 13:24
Boston
Logan
 5h 9m
layover
1h 37m - Newark
 United Airlines
UA563
UA408
from $211
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10:35
Chicago
O'Hare International
 16:28
Boston
Logan
 4h 53m
layover
1h 18m - Newark
 United Airlines
UA1126
UA2033
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 18, 2025
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
06:00 — 13:24
06:00 — 09:15 UA1658 United Airlines
Chicago — Newark
2h 55m stop
12:10 — 13:24 UA408 United Airlines
Newark — Boston
6h 24m
including layover
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from$134
06:30 — 09:56
06:30 — 09:56 UA2104 United Airlines
Chicago — Boston
2h 26m
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from$103
07:15 — 13:24
07:15 — 10:33 UA563 United Airlines
Chicago — Newark
1h 37m stop
12:10 — 13:24 UA408 United Airlines
Newark — Boston
5h 9m
including layover
Find flight
from$134
09:13 — 12:48
09:13 — 12:48 UA536 United Airlines
Chicago — Boston
2h 35m
Find flight
from$101
10:35 — 16:28
10:35 — 13:52 UA1126 United Airlines
Chicago — Newark
1h 18m stop
15:10 — 16:28 UA2033 United Airlines
Newark — Boston
4h 53m
including layover
Find flight
from$211
11:05 — 14:40
11:05 — 14:40 UA399 United Airlines
Chicago — Boston
2h 35m
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from$261
13:12 — 16:43
13:12 — 16:43 UA2022 United Airlines
Chicago — Boston
2h 31m
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from$158
14:15 — 17:46
14:15 — 17:46 UA664 United Airlines
Chicago — Boston
2h 31m
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from$158
14:20 — 23:08
14:20 — 17:47 UA2649 United Airlines
Chicago — Newark
3h 58m stop
21:45 — 23:08 UA1395 United Airlines
Newark — Boston
7h 48m
including layover
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from$134
15:48 — 19:19
15:48 — 19:19 UA1677 United Airlines
Chicago — Boston
2h 31m
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from$461
17:03 — 23:08
16:50 — 20:17 UA1276 United Airlines
Chicago — Newark
1h 15m stop
21:45 — 23:08 UA1395 United Airlines
Newark — Boston
5h 5m
including layover
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from$242
17:55 — 23:57
17:56 — 20:55 UA2677 United Airlines
Chicago — Washington D.C.
1h 23m stop
22:18 — 23:59 UA755 United Airlines
Washington D.C. — Boston
5h 2m
including layover
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from$140
17:57 — 21:28
17:57 — 21:28 UA1531 United Airlines
Chicago — Boston
2h 31m
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from$130
20:12 — 11:18
+1 day
20:12 — 00:20 NK2126 Spirit Airlines
Chicago — Miami
7h 45m stop
08:05 — 11:18 NK2300 Spirit Airlines
Miami — Boston
14h 6m
including layover
Find flight
from$240
21:15 — 00:45
+1 day
21:15 — 00:45 UA1779 United Airlines
Chicago — Boston
2h 30m
Find flight
from$389
*Departure and arrival times - local. Updated on September 18, 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 23:45 from 7 Chicago airports and arrive 05:05 to 23:45 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 23:45
  • Distance 852 ml

The cheapest months to travel to Boston are may (from 90 $), september (from 90 $), july (from 100 $).

The most expensive months are november (from 4 000 $), october (from 103 $), august (from 101 $).

What is the lowest airfare Chicago to Boston?

The cheapest plane ticket found by our users is $101. This airfare is for economy class on one-way UA536 flight by United Airlines for August 25, 2025 which leaves O'Hare International in Chicago at 09:13 am and arrives at Boston Logan at 12:48.

Economy class
$101
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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 6 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Frontier Airlines - 8 departures per week at the price of from $ 347 . And the most expensive tickets are offered by Turkish Airlines airline - from $ 4450.

Direct flights

There are 8 nonstop flights on the route. The fastest direct flight is UA2104 by United Airlines takes 2h 26m and the cheapest is UA536 by United Airlines for $101.

  • UA - United Airlines
    from $101
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Connecting Flights

There are 63 flights with layovers on the route. The fastest connecting flight is UA2029 by United Airlines takes 4h 23m and the cheapest is UA536 by United Airlines for $134.

  • F9 - Frontier Airlines
    from $347
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  • TK - Turkish Airlines
    from $4450
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  • AY - Finnair
    from $1874
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  • UA - United Airlines
    from $134
    Find
  • NK - Spirit Airlines
    from $240
    Find
  • G4 - Allegiant Air
    from $281
    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 $101
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  • Midway-MDW
    from $281
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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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Airplanes

There are flights to Boston from Chicago by 6 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Chicago

You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.

Top International Destinations from Chicago

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

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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