Cheap Flights from Chicago, IL to Boston, MA from $43

One way Round trip

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On Cheapflightsplus.com you will find 33 direct and 580 connecting flights from Chicago to Boston. You can compare airfare deals from 17 airlines and multiple travel sites from $43, 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: $43 (one-way), $74 (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 $43. The fastest direct flight takes 2h 13m and the fastest connecting – 3h 53m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $43 Find flight	16:38 Chicago O'Hare International	19:57 Boston Logan	2h 19m	Spirit Airlines	NK177
from $70 Find flight	07:22 Chicago O'Hare International	10:41 Boston Logan	2h 19m	United Airlines	UA2454
from $74 Find flight	08:10 Chicago O'Hare International	11:23 Boston Logan	2h 13m	American Airlines	AA314
from $83 Find flight	06:40 Chicago O'Hare International	10:00 Boston Logan	2h 20m	Delta Air Lines Inc.	DL2956
from $98 Find flight	16:53 Chicago O'Hare International	20:14 Boston Logan	2h 21m	JetBlue	B6612
from $99 Find flight	15:35 Chicago O'Hare International	18:56 Boston Logan	2h 21m	United Airlines	UA1719
from $112 Find flight	07:00 Chicago O'Hare International	10:20 Boston Logan	2h 20m	American Airlines	AA3703
from $115 Find flight	14:05 Chicago O'Hare International	17:30 Boston Logan	2h 25m	Delta Air Lines Inc.	DL2679
from $126 Find flight	21:35 Chicago O'Hare International	00:54+1 день Boston Logan	2h 19m	United Airlines	UA2627
from $135 Find flight	12:50 Chicago O'Hare International	16:09 Boston Logan	2h 19m	United Airlines	UA1332
from $62 Find flight	16:18 Chicago O'Hare International	00:35+1 день Boston Logan	7h 17m layover 2h 28m - Atlanta	Frontier Airlines	F91596 F93512
from $62 Find flight	14:35 Chicago Midway	00:35+1 день Boston Logan	9h 0m layover 4h 21m - Atlanta	Frontier Airlines	F92144 F93512
from $62 Find flight	13:11 Chicago O'Hare International	00:36+1 день Boston Logan	10h 25m layover 4h 18m - Orlando	Frontier Airlines	F92792 F91978
from $65 Find flight	21:55 Chicago O'Hare International	08:49+1 день Boston Logan	9h 54m layover 5h 22m - Atlanta	Frontier Airlines	F91442 F93086
from $69 Find flight	14:28 Chicago O'Hare International	23:32 Boston Logan	8h 4m layover 1h 37m - Miami	Spirit Airlines	NK717 NK866
from $72 Find flight	16:01 Chicago O'Hare International	00:27+1 день Boston Logan	7h 26m layover 1h 25m - Orlando	Frontier Airlines	F93044 F91978

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 01, 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
06:40 — 10:00	06:40 — 10:00 DL2956 Delta Air Lines Inc. Chicago — Boston	2h 20m	Find flight from$83
07:00 — 10:20	07:00 — 10:20 AA3703 American Airlines Chicago — Boston	2h 20m	Find flight from$112
07:22 — 10:41	07:22 — 10:41 UA2454 United Airlines Chicago — Boston	2h 19m	Find flight from$70
07:30 — 10:49	07:30 — 10:49 UA592 United Airlines Chicago — Boston	2h 19m	Find flight from$110
07:30 — 10:56	07:30 — 10:56 UA1083 United Airlines Chicago — Boston	2h 26m	Find flight from$135
07:30 — 10:49	07:30 — 10:49 UA414 United Airlines Chicago — Boston	2h 19m	Find flight from$271
07:46 — 11:12	07:46 — 11:12 UA1450 United Airlines Chicago — Boston	2h 26m	Find flight from$265
08:10 — 11:23	08:10 — 11:23 AA314 American Airlines Chicago — Boston	2h 13m	Find flight from$74
08:41 — 12:03	08:41 — 12:03 B6312 JetBlue Chicago — Boston	2h 22m	Find flight from$98
09:15 — 12:38	09:15 — 12:38 UA307 United Airlines Chicago — Boston	2h 23m	Find flight from$271
09:20 — 12:45	09:20 — 12:45 UA217 United Airlines Chicago — Boston	2h 25m	Find flight from$111
09:20 — 12:46	09:20 — 12:46 UA691 United Airlines Chicago — Boston	2h 26m	Find flight from$135
09:25 — 12:50	09:25 — 12:50 UA2099 United Airlines Chicago — Boston	2h 25m	Find flight from$127
10:25 — 13:55	10:25 — 13:55 DL2391 Delta Air Lines Inc. Chicago — Boston	2h 30m	Find flight from$115
11:08 — 14:27	11:08 — 14:27 UA399 United Airlines Chicago — Boston	2h 19m	Find flight from$131
12:30 — 15:50	12:30 — 15:50 AA4384 American Airlines Chicago — Boston	2h 20m	Find flight from$314
12:50 — 16:09	12:50 — 16:09 UA1332 United Airlines Chicago — Boston	2h 19m	Find flight from$135
13:55 — 17:16	13:55 — 17:16 UA580 United Airlines Chicago — Boston	2h 21m	Find flight from$110
14:05 — 17:30	14:05 — 17:30 DL2679 Delta Air Lines Inc. Chicago — Boston	2h 25m	Find flight from$115
14:50 — 18:07	14:50 — 18:07 AA3690 American Airlines Chicago — Boston	2h 17m	Find flight from$274
15:35 — 18:56	15:35 — 18:56 UA1719 United Airlines Chicago — Boston	2h 21m	Find flight from$99
16:00 — 19:21	16:00 — 19:21 UA470 United Airlines Chicago — Boston	2h 21m	Find flight from$110
16:00 — 19:13	16:00 — 19:13 AA1219 American Airlines Chicago — Boston	2h 13m	Find flight from$137
16:00 — 19:19	16:00 — 19:19 UA2475 United Airlines Chicago — Boston	2h 19m	Find flight from$271
16:15 — 19:38	16:15 — 19:38 UA2658 United Airlines Chicago — Boston	2h 23m	Find flight from$189
16:38 — 19:57	16:38 — 19:57 NK177 Spirit Airlines Chicago — Boston	2h 19m	Find flight from$43
16:53 — 20:14	16:53 — 20:14 B6612 JetBlue Chicago — Boston	2h 21m	Find flight from$98
18:25 — 21:50	18:25 — 21:50 UA1742 United Airlines Chicago — Boston	2h 25m	Find flight from$110
18:25 — 21:54	18:25 — 21:54 UA715 United Airlines Chicago — Boston	2h 29m	Find flight from$240
18:35 — 21:59	18:35 — 21:59 UA1989 United Airlines Chicago — Boston	2h 24m	Find flight from$135
18:50 — 22:22	18:50 — 22:22 DL2646 Delta Air Lines Inc. Chicago — Boston	2h 32m	Find flight from$115
20:20 — 23:44	20:20 — 23:44 AA4380 American Airlines Chicago — Boston	2h 24m	Find flight from$137
21:35 — 00:54 +1 day	21:35 — 00:54 UA2627 United Airlines Chicago — Boston	2h 19m	Find flight from$126
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$102
07:00 — 10:46 +1 day	07:00 — 10:43 F91416 Frontier Airlines Chicago — Tampa 21h 2m stop 07:45 — 10:46 F91216 Frontier Airlines Tampa — Boston	26h 46m including layover	Find flight from$77
08:00 — 18:25	08:00 — 11:50 NK1686 Spirit Airlines Chicago — Orlando 3h 32m stop 15:22 — 18:25 NK794 Spirit Airlines Orlando — Boston	9h 25m including layover	Find flight from$69
09:48 — 18:36	09:48 — 12:59 B6906 JetBlue Chicago — New York 4h 11m stop 17:10 — 18:36 B61418 JetBlue New York — Boston	7h 48m including layover	Find flight from$101
10:58 — 00:27 +1 day	20:20 — 00:16 F91458 Frontier Airlines Chicago — Orlando 6h 38m stop 21:30 — 00:36 F91978 Frontier Airlines Orlando — Boston	12h 29m including layover	Find flight from$76
10:59 — 00:27 +1 day	10:59 — 14:51 F92042 Frontier Airlines Chicago — Orlando 6h 32m stop 21:23 — 00:27 F91978 Frontier Airlines Orlando — Boston	12h 28m including layover	Find flight from$77
12:00 — 21:54	08:00 — 11:50 NK1686 Spirit Airlines Chicago — Orlando 3h 3m stop 18:50 — 21:54 NK2989 Spirit Airlines Orlando — Boston	8h 54m including layover	Find flight from$69
13:11 — 00:36 +1 day	13:11 — 17:12 F92792 Frontier Airlines Chicago — Orlando 4h 18m stop 21:30 — 00:36 F91978 Frontier Airlines Orlando — Boston	10h 25m including layover	Find flight from$62
14:28 — 23:32	14:28 — 18:43 NK717 Spirit Airlines Chicago — Miami 1h 37m stop 20:20 — 23:32 NK866 Spirit Airlines Miami — Boston	8h 4m including layover	Find flight from$69
14:35 — 00:35 +1 day	11:59 — 15:15 F92144 Frontier Airlines Chicago — Atlanta 4h 21m stop 22:00 — 00:29 F93512 Frontier Airlines Atlanta — Boston	9h including layover	Find flight from$62
15:31 — 00:31 +1 day	14:19 — 17:17 F94148 Frontier Airlines Chicago — Philadelphia 4h 29m stop 22:59 — 00:31 F93012 Frontier Airlines Philadelphia — Boston	8h including layover	Find flight from$76
16:18 — 00:35 +1 day	14:27 — 17:35 F91596 Frontier Airlines Chicago — Atlanta 2h 28m stop 22:00 — 00:29 F93512 Frontier Airlines Atlanta — Boston	7h 17m including layover	Find flight from$62
19:45 — 09:51 +1 day	19:45 — 23:50 NK1841 Spirit Airlines Chicago — Orlando 7h stop 06:50 — 09:51 NK2068 Spirit Airlines Orlando — Boston	13h 6m including layover	Find flight from$91
19:46 — 09:24 +1 day	19:46 — 23:54 NK158 Spirit Airlines Chicago — Miami 6h 21m stop 06:15 — 09:24 NK1987 Spirit Airlines Miami — Boston	12h 38m including layover	Find flight from$90
21:01 — 11:46 +1 day	21:01 — 23:42 F93243 Frontier Airlines Chicago — Dallas 7h 30m stop 07:12 — 11:46 F93602 Frontier Airlines Dallas — Boston	13h 45m including layover	Find flight from$77
21:55 — 08:49 +1 day	21:55 — 00:58 F91442 Frontier Airlines Chicago — Atlanta 5h 22m stop 06:20 — 08:49 F93086 Frontier Airlines Atlanta — Boston	9h 54m including layover	Find flight from$65

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

*Departure and arrival times - local. Updated on April 1, 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 05:00 to 22:13 from 7 Chicago airports and arrive 05:00 to 22:13 to 4 Boston airports. Average flight time is 2h 21m.

The fastest flight 2h 13m
Average flight time 2h 21m
The earliest flight 05:00
The latest flight 22:13
Distance 852 ml

The cheapest months to travel to Boston are november (from 43 $), january (from 69 $), december (from 76 $).

The most expensive months are february (from 97 $), december (from 76 $), january (from 69 $).

What is the lowest airfare Chicago to Boston?

The cheapest plane ticket found by our users is $43. This airfare is for economy class on one-way NK177 flight by Spirit Airlines for November 15, 2024 which leaves O'Hare International in Chicago at 16:38 am and arrives at Boston Logan at 19:57.

Economy class

$43

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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 17 regular airlines and 7 low-cost airlines. Most of the flights on this route are operated by Delta Air Lines Inc. - 84 departures per week at the price of from $ 83 . And the most expensive tickets are offered by SWISS International Air Lines airline - from $ 6607.

Direct flights

There are 33 nonstop flights on the route. The fastest direct flight is AA314 by American Airlines takes 2h 13m and the cheapest is NK177 by Spirit Airlines for $43.

B6 - JetBlue

from $98

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DL - Delta Air Lines Inc.

from $83

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UA - United Airlines

from $70

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NK - Spirit Airlines

from $43

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AA - American Airlines

from $74

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See more direct flights

Connecting Flights

There are 580 flights with layovers on the route. The fastest connecting flight is DL2039 by Delta Air Lines Inc. takes 3h 53m and the cheapest is NK177 by Spirit Airlines for $62.

DL - Delta Air Lines Inc.

from $168

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UA - United Airlines

from $111

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B6 - JetBlue

from $101

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NK - Spirit Airlines

from $69

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AA - American Airlines

from $145

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EI - Aer Lingus

from $1346

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SY - Sun Country Airlines

from $328

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LX - SWISS International Air Lines

from $6580

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G4 - Allegiant Air

from $501

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AS - Alaska Airlines

from $244

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F9 - Frontier Airlines

from $62

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PD - Porter Airlines

from $312

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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 $43
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Midway-MDW

from $62
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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 17 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737-800

from $74

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Airbus A320

from $83

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Embraer Lineage 1000

from $98

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Airbus A318

from $101

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Airbus A321

from $108

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Embraer 175 (short wing)

from $112

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Boeing 737-100/200

from $118

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Embraer 175

from $140

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Airbus A319

from $165

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Boeing 737-900

from $169

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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

Find
Chicago — New York

from $74

Find
Chicago — Atlanta

from $76

Find
Chicago — Orlando

from $62

Find
Chicago — Miami

from $66

Find
Chicago — Dallas

from $70

Find
Chicago — Houston

from $66

Find
Chicago — Boston

from $61

Find
Chicago — Phoenix

from $65

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Chicago — Denver

from $61

Find

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 — Cancun

from $72

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Chicago — Toronto

from $73

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Chicago — Paris

from $61

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Chicago — Rome

from $79

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Chicago — Hyderabad

from $73

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Chicago — Mexico City

from $76

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Chicago — Tokyo

from $60

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Chicago — Dublin

from $59

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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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