Cheap Flights from Chicago, IL to Boston, MA from $91

One way Round trip

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On Cheapflightsplus.com you will find 4 direct and 27 connecting flights from Chicago to Boston. You can compare airfare deals from 4 airlines and multiple travel sites from $91, 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: $91 (one-way), $156 (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 $91. The fastest direct flight takes 2h 19m and the fastest connecting – 4h 35m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $121 Find flight	18:35 Chicago O'Hare International	21:59 Boston Logan	2h 24m	United Airlines	UA1989
from $241 Find flight	07:30 Chicago O'Hare International	10:49 Boston Logan	2h 19m	United Airlines	UA414
from $241 Find flight	16:00 Chicago O'Hare International	19:19 Boston Logan	2h 19m	United Airlines	UA2475
from $241 Find flight	09:15 Chicago O'Hare International	12:38 Boston Logan	2h 23m	United Airlines	UA307
from $91 Find flight	05:01 Chicago O'Hare International	11:46 Boston Logan	5h 45m layover 2h 17m - Philadelphia	Frontier Airlines	F92112 F93012
from $111 Find flight	16:20 Chicago O'Hare International	00:39+1 день Boston Logan	7h 19m layover 0h 55m - Miami	Spirit Airlines	NK1 NK616
from $131 Find flight	18:14 Chicago O'Hare International	23:59 Boston Logan	4h 45m layover 1h 15m - Washington D.C.	United Airlines	UA444 UA755
from $131 Find flight	06:00 Chicago O'Hare International	12:05 Boston Logan	5h 5m layover 1h 50m - Newark	United Airlines	UA2343 UA1864
from $135 Find flight	19:59 Chicago Midway	06:55+1 день Boston Logan	9h 56m layover 6h 18m - Philadelphia	Frontier Airlines	F91618 F92168
from $135 Find flight	20:54 Chicago Midway	12:00+1 день Boston Logan	14h 6m layover 7h 51m - Dallas	Frontier Airlines	F92881 F93602
from $135 Find flight	12:15 Chicago Midway	09:20+1 день Boston Logan	20h 5m layover 16h 12m - Raleigh	Frontier Airlines	F93718 F93058
from $183 Find flight	08:00 Chicago O'Hare International	07:55+1 день Boston Logan	22h 55m layover 18h 44m - Charlotte	Frontier Airlines	F93142 F93614
from $250 Find flight	11:53 Chicago O'Hare International	17:28 Boston Logan	4h 35m layover 1h 7m - Newark	United Airlines	UA2488 UA1835
from $250 Find flight	11:53 Chicago O'Hare International	18:31 Boston Logan	5h 38m layover 2h 7m - Newark	United Airlines	UA2488 UA2612
from $250 Find flight	16:10 Chicago O'Hare International	23:59 Boston Logan	6h 49m layover 3h 23m - Washington D.C.	United Airlines	UA587 UA755
from $189 Find flight	07:20 Chicago O'Hare International	22:12 Boston Logan	13h 52m layover 1h 22m - Dallas 5h 30m - Atlanta	Spirit Airlines	NK824 NK825 NK1180

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on February 22, 2025

Flight Schedule Chicago (Illinois) to Boston (Massachusetts)

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	Flight Details	Flight Duration	Price
07:30 — 10:49	07:30 — 10:49 UA414 United Airlines Chicago — Boston	2h 19m	Find flight from$241
09:15 — 12:38	09:15 — 12:38 UA307 United Airlines Chicago — Boston	2h 23m	Find flight from$241
16:00 — 19:19	16:00 — 19:19 UA2475 United Airlines Chicago — Boston	2h 19m	Find flight from$241
18:35 — 21:59	18:35 — 21:59 UA1989 United Airlines Chicago — Boston	2h 24m	Find flight from$121
05:01 — 11:46	05:01 — 08:04 F92112 Frontier Airlines Chicago — Philadelphia 2h 17m stop 10:21 — 11:46 F93012 Frontier Airlines Philadelphia — Boston	5h 45m including layover	Find flight from$91
06:00 — 12:05	06:00 — 09:11 UA2343 United Airlines Chicago — Newark 1h 50m stop 10:55 — 12:07 UA1864 United Airlines Newark — Boston	5h 5m including layover	Find flight from$131
06:00 — 16:33	06:00 — 09:05 UA2343 United Airlines Chicago — Newark 6h 15m stop 15:20 — 16:33 UA2136 United Airlines Newark — Boston	9h 33m including layover	Find flight from$295
08:00 — 07:55 +1 day	08:00 — 11:01 F93142 Frontier Airlines Chicago — Charlotte 18h 44m stop 05:45 — 07:55 F93614 Frontier Airlines Charlotte — Boston	22h 55m including layover	Find flight from$183
09:03 — 16:33	09:03 — 12:18 UA1213 United Airlines Chicago — Newark 3h 2m stop 15:20 — 16:33 UA2136 United Airlines Newark — Boston	6h 30m including layover	Find flight from$340
10:00 — 23:59	10:00 — 12:43 AS462 Alaska Airlines Chicago — Seattle 3h 2m stop 15:45 — 23:59 AS460 Alaska Airlines Seattle — Boston	12h 59m including layover	Find flight from$309
10:53 — 16:33	10:53 — 14:05 UA2091 United Airlines Chicago — Newark 1h 15m stop 15:20 — 16:33 UA2136 United Airlines Newark — Boston	4h 40m including layover	Find flight from$340
11:53 — 17:28	11:53 — 15:08 UA2488 United Airlines Chicago — Newark 1h 7m stop 16:15 — 17:28 UA1835 United Airlines Newark — Boston	4h 35m including layover	Find flight from$250
11:53 — 18:31	11:53 — 15:08 UA2488 United Airlines Chicago — Newark 2h 7m stop 17:15 — 18:31 UA2612 United Airlines Newark — Boston	5h 38m including layover	Find flight from$250
12:15 — 09:20 +1 day	12:15 — 15:10 F93718 Frontier Airlines Chicago — Raleigh 16h 12m stop 07:22 — 09:20 F93058 Frontier Airlines Raleigh — Boston	20h 5m including layover	Find flight from$135
16:20 — 00:39 +1 day	13:40 — 17:46 NK1 Spirit Airlines Chicago — Miami 55m stop 20:15 — 23:27 NK616 Spirit Airlines Miami — Boston	7h 19m including layover	Find flight from$111
17:42 — 08:31 +1 day	17:42 — 21:31 NK507 Spirit Airlines Chicago — Orlando 7h 59m stop 05:30 — 08:31 NK1848 Spirit Airlines Orlando — Boston	13h 49m including layover	Find flight from$283
17:54 — 07:44 +1 day	17:54 — 20:35 AS353 Alaska Airlines Chicago — Seattle 2h 55m stop 23:30 — 07:44 AS536 Alaska Airlines Seattle — Boston	12h 50m including layover	Find flight from$316
18:14 — 23:59	18:08 — 21:00 UA444 United Airlines Chicago — Washington D.C. 1h 15m stop 22:24 — 23:59 UA755 United Airlines Washington D.C. — Boston	4h 45m including layover	Find flight from$131
19:59 — 06:55 +1 day	19:59 — 23:12 F91618 Frontier Airlines Chicago — Philadelphia 6h 18m stop 05:30 — 06:55 F92168 Frontier Airlines Philadelphia — Boston	9h 56m including layover	Find flight from$135
20:15 — 09:50 +1 day	20:15 — 23:28 UA1655 United Airlines Chicago — Newark 9h 4m stop 08:32 — 09:50 UA559 United Airlines Newark — Boston	12h 35m including layover	Find flight from$268
20:54 — 12:00 +1 day	20:54 — 23:24 F92881 Frontier Airlines Chicago — Dallas 7h 51m stop 07:15 — 12:00 F93602 Frontier Airlines Dallas — Boston	14h 6m including layover	Find flight from$135
21:40 — 09:50 +1 day	21:40 — 00:45 UA1633 United Airlines Chicago — Newark 7h 47m stop 08:32 — 09:50 UA559 United Airlines Newark — Boston	11h 10m including layover	Find flight from$268
21:40 — 12:05 +1 day	21:40 — 00:45 UA1633 United Airlines Chicago — Newark 10h 10m stop 10:55 — 12:05 UA1864 United Airlines Newark — Boston	13h 25m including layover	Find flight from$295
05:05 — 23:29	05:05 — 09:10 NK19 Spirit Airlines Chicago — Miami 5h 14m stop 14:24 — 16:59 NK120 Spirit Airlines Miami — Baltimore 5h stop 21:59 — 23:29 NK2075 Spirit Airlines Baltimore — Boston	17h 24m including layover	Find flight from$356
07:20 — 22:12	07:20 — 09:33 NK824 Spirit Airlines Chicago — Dallas 1h 22m stop 10:55 — 14:00 NK825 Spirit Airlines Dallas — Atlanta 5h 30m stop 19:30 — 22:12 NK1180 Spirit Airlines Atlanta — Boston	13h 52m including layover	Find flight from$189
08:30 — 23:29	08:30 — 12:37 NK1986 Spirit Airlines Chicago — Miami 3h 16m stop 15:53 — 18:28 NK224 Spirit Airlines Miami — Baltimore 3h 31m stop 21:59 — 23:29 NK2075 Spirit Airlines Baltimore — Boston	13h 59m including layover	Find flight from$356

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on February 22, 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 05:01 to 21:40 from 7 Chicago airports and arrive 05:01 to 21:40 to 4 Boston airports. Average flight time is 2h 21m.

The fastest flight 2h 19m
Average flight time 2h 21m
The earliest flight 05:01
The latest flight 21:40
Distance 852 ml

The cheapest months to travel to Boston are february (from 91 $), november (from 111 $), january (from 121 $).

The most expensive months are december (from 299 $), january (from 121 $), november (from 111 $).

What is the lowest airfare Chicago to Boston?

The cheapest plane ticket found by our users is $91. This airfare is for economy class on one-way F92112 flight by Frontier Airlines for February 21, 2025 which leaves O'Hare International in Chicago at 05:01 am and arrives at Boston Logan at 11:46.

Economy class

$91

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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 4 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 2 departures per week at the price of from $ 309 . And the most expensive tickets are offered by Spirit Airlines airline - from $ 360.

Direct flights

There are 4 nonstop flights on the route. The fastest direct flight is UA414 by United Airlines takes 2h 19m and the cheapest is F92112 by Frontier Airlines for $121.

UA - United Airlines

from $121

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Connecting Flights

There are 27 flights with layovers on the route. The fastest connecting flight is UA2488 by United Airlines takes 4h 35m and the cheapest is F92112 by Frontier Airlines for $91.

AS - Alaska Airlines

from $309

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F9 - Frontier Airlines

from $91

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UA - United Airlines

from $131

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NK - Spirit Airlines

from $111

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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 $91
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Midway-MDW

from $135
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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 4 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.

Chicago — Las Vegas

from $508

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from $63

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Chicago — Los Angeles

from $181

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Chicago — Orlando

from $62

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Chicago — New York

from $74

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Chicago — Dallas

from $70

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Chicago — San Antonio

from $59

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Chicago — Atlanta

from $76

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Chicago — Miami

from $66

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Chicago — Denver

from $61

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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.

Chicago — London

from $60

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Chicago — Manchester

from $58

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Chicago — Zurich

from $61

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Chicago — Cancun

from $72

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Chicago — Dublin

from $59

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Chicago — Madrid

from $72

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Chicago — Rome

from $79

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Chicago — Paris

from $61

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Chicago — Tel Aviv

from $628

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Chicago — Mumbai

from $74

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How to book a plane 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.
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