Cheap Flights from Boston, MA to Chicago, IL from $56

One way Round trip

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Price Calendar Cheap Flights Flights Schedule

On Cheapflightsplus.com you will find 30 direct and 545 connecting flights from Boston to Chicago. You can compare airfare deals from 15 airlines and multiple travel sites from $56, 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: $56 (one-way), $96 (round-trip).

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Best Flights from Boston to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Boston to Chicago with the lowest price of $56. The fastest direct flight takes 2h 45m and the fastest connecting – 4h 30m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $57 Find flight	06:00 Boston Logan	08:06 Chicago O'Hare International	3h 6m	JetBlue	B6311
from $63 Find flight	06:00 Boston Logan	07:56 Chicago O'Hare International	2h 56m	United Airlines	UA1414
from $67 Find flight	12:00 Boston Logan	14:01 Chicago O'Hare International	3h 1m	American Airlines	AA1239
from $72 Find flight	09:45 Boston Logan	11:53 Chicago O'Hare International	3h 8m	Spirit Airlines	NK174
from $75 Find flight	19:50 Boston Logan	21:51 Chicago O'Hare International	3h 1m	Delta Air Lines Inc.	DL2676
from $78 Find flight	07:00 Boston Logan	08:45 Chicago Midway	2h 45m	Southwest Airlines	WN787
from $82 Find flight	11:05 Boston Logan	13:03 Chicago O'Hare International	2h 58m	Delta Air Lines Inc.	DL2679
from $100 Find flight	09:30 Boston Logan	11:26 Chicago O'Hare International	2h 56m	United Airlines	UA378
from $101 Find flight	17:15 Boston Logan	19:22 Chicago O'Hare International	3h 7m	American Airlines	AA4629
from $122 Find flight	09:30 Boston Logan	11:28 Chicago O'Hare International	2h 58m	United Airlines	UA216
from $56 Find flight	06:00 Boston Logan	13:54 Chicago Midway	8h 54m layover 2h 21m - Orlando	Frontier Airlines	F91977 F91457
from $56 Find flight	12:00 Boston Logan	20:15 Chicago O'Hare International	9h 15m layover 2h 45m - Orlando	Spirit Airlines	NK2071 NK1147
from $56 Find flight	10:34 Boston Logan	21:07 Chicago O'Hare International	11h 33m layover 4h 39m - Miami	Spirit Airlines	NK1988 NK7
from $67 Find flight	11:35 Boston Logan	22:41 Chicago Midway	12h 6m layover 5h 42m - Dallas	Frontier Airlines	F93601 F92882
from $87 Find flight	06:00 Boston Logan	22:55 Chicago O'Hare International	17h 55m layover 2h 28m - Orlando 6h 38m - New York	Spirit Airlines	NK2990 NK204 NK225
from $102 Find flight	16:25 Boston Logan	09:52+1 день Chicago O'Hare International	18h 27m layover 2h 17m - Atlanta 7h 42m - Miami	Spirit Airlines	NK1363 NK501 NK1986

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on November 06, 2024

Flight Schedule Boston (Massachusetts) to Chicago (Illinois)

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	Flight Details	Flight Duration	Price
05:15 — 07:19	05:15 — 07:19 AA3452 American Airlines Boston — Chicago	3h 4m	Find flight from$67
06:00 — 08:06	06:00 — 08:06 B6311 JetBlue Boston — Chicago	3h 6m	Find flight from$57
06:00 — 07:56	06:00 — 07:56 UA1414 United Airlines Boston — Chicago	2h 56m	Find flight from$63
07:00 — 08:45	07:00 — 08:45 WN787 Southwest Airlines Boston — Chicago	2h 45m	Find flight from$78
07:20 — 09:29	07:20 — 09:29 DL2570 Delta Air Lines Inc. Boston — Chicago	3h 9m	Find flight from$75
09:20 — 11:22	09:20 — 11:22 UA260 United Airlines Boston — Chicago	3h 2m	Find flight from$124
09:30 — 11:26	09:30 — 11:26 UA1684 United Airlines Boston — Chicago	2h 56m	Find flight from$63
09:30 — 11:26	09:30 — 11:26 UA378 United Airlines Boston — Chicago	2h 56m	Find flight from$100
09:30 — 11:28	09:30 — 11:28 UA216 United Airlines Boston — Chicago	2h 58m	Find flight from$122
09:45 — 11:53	09:45 — 11:53 NK174 Spirit Airlines Boston — Chicago	3h 8m	Find flight from$72
10:30 — 12:31	10:30 — 12:31 AA3569 American Airlines Boston — Chicago	3h 1m	Find flight from$124
10:45 — 12:41	10:45 — 12:41 UA1631 United Airlines Boston — Chicago	2h 56m	Find flight from$63
10:52 — 12:54	10:52 — 12:54 UA1823 United Airlines Boston — Chicago	3h 2m	Find flight from$124
10:57 — 12:55	10:57 — 12:55 UA267 United Airlines Boston — Chicago	2h 58m	Find flight from$122
11:05 — 13:03	11:05 — 13:03 DL2679 Delta Air Lines Inc. Boston — Chicago	2h 58m	Find flight from$82
12:00 — 14:01	12:00 — 14:01 AA1239 American Airlines Boston — Chicago	3h 1m	Find flight from$67
12:12 — 14:10	12:12 — 14:10 UA222 United Airlines Boston — Chicago	2h 58m	Find flight from$122
12:25 — 14:21	12:25 — 14:21 UA1732 United Airlines Boston — Chicago	2h 56m	Find flight from$100
13:29 — 15:36	13:29 — 15:36 AA4392 American Airlines Boston — Chicago	3h 7m	Find flight from$67
14:14 — 16:08	14:14 — 16:08 B6611 JetBlue Boston — Chicago	2h 54m	Find flight from$136
14:41 — 16:43	14:41 — 16:43 AA514 American Airlines Boston — Chicago	3h 2m	Find flight from$67
15:14 — 17:10	15:14 — 17:10 UA519 United Airlines Boston — Chicago	2h 56m	Find flight from$233
15:45 — 17:46	15:45 — 17:46 DL2646 Delta Air Lines Inc. Boston — Chicago	3h 1m	Find flight from$82
16:23 — 18:19	16:23 — 18:19 UA2040 United Airlines Boston — Chicago	2h 56m	Find flight from$63
17:15 — 19:22	17:15 — 19:22 AA4629 American Airlines Boston — Chicago	3h 7m	Find flight from$101
18:00 — 19:45	18:00 — 19:45 WN1549 Southwest Airlines Boston — Chicago	2h 45m	Find flight from$78
18:25 — 20:25	18:25 — 20:25 UA1015 United Airlines Boston — Chicago	3h	Find flight from$242
18:28 — 20:24	18:28 — 20:24 UA1134 United Airlines Boston — Chicago	2h 56m	Find flight from$63
19:50 — 21:51	19:50 — 21:51 DL2676 Delta Air Lines Inc. Boston — Chicago	3h 1m	Find flight from$75
19:59 — 21:55	19:59 — 21:55 UA1783 United Airlines Boston — Chicago	2h 56m	Find flight from$168
05:00 — 16:06	06:00 — 09:31 NK296 Spirit Airlines Boston — Miami 5h 14m stop 16:20 — 18:41 NK157 Spirit Airlines Miami — Chicago	12h 6m including layover	Find flight from$56
06:00 — 13:54	06:00 — 09:31 F91977 Frontier Airlines Boston — Orlando 2h 21m stop 06:00 — 07:55 F91457 Frontier Airlines Orlando — Chicago	8h 54m including layover	Find flight from$56
09:39 — 16:56	09:39 — 12:45 F93511 Frontier Airlines Boston — Atlanta 2h 55m stop 15:40 — 16:56 F92007 Frontier Airlines Atlanta — Chicago	8h 17m including layover	Find flight from$58
10:34 — 21:07	10:23 — 13:52 NK1988 Spirit Airlines Boston — Miami 4h 39m stop 18:45 — 21:08 NK7 Spirit Airlines Miami — Chicago	11h 33m including layover	Find flight from$56
11:24 — 00:38 +1 day	11:24 — 14:50 F93601 Frontier Airlines Boston — Dallas 7h 27m stop 22:17 — 00:38 F93244 Frontier Airlines Dallas — Chicago	14h 14m including layover	Find flight from$56
11:26 — 20:13	11:26 — 15:03 NK2975 Spirit Airlines Boston — Miami 2h 47m stop 17:50 — 20:13 NK19 Spirit Airlines Miami — Chicago	9h 47m including layover	Find flight from$62
12:00 — 20:15	11:30 — 14:57 NK2071 Spirit Airlines Boston — Orlando 2h 45m stop 18:05 — 20:15 NK1147 Spirit Airlines Orlando — Chicago	9h 15m including layover	Find flight from$56
12:38 — 21:02	11:24 — 14:50 F93601 Frontier Airlines Boston — Dallas 2h 37m stop 19:50 — 22:14 F92998 Frontier Airlines Dallas — Chicago	9h 24m including layover	Find flight from$56
13:00 — 22:06	13:00 — 14:16 AA4342 American Airlines Boston — New York 6h 13m stop 20:29 — 22:06 NK3386 Spirit Airlines New York — Chicago	10h 6m including layover	Find flight from$96
14:18 — 20:58	14:18 — 17:43 NK502 Spirit Airlines Boston — Orlando 1h 11m stop 18:54 — 20:58 NK1842 Spirit Airlines Orlando — Chicago	7h 40m including layover	Find flight from$82
15:55 — 23:11	15:55 — 19:40 NK1578 Spirit Airlines Boston — Fort Myers 1h 30m stop 21:10 — 23:11 NK488 Spirit Airlines Fort Myers — Chicago	8h 16m including layover	Find flight from$97
19:38 — 23:20	19:38 — 21:25 UA2136 United Airlines Boston — Washington D.C. 51m stop 22:16 — 23:20 UA1738 United Airlines Washington D.C. — Chicago	4h 42m including layover	Find flight from$97

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

*Departure and arrival times - local. Updated on November 6, 2024

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 05:00 to 22:50 from 4 Boston airports and arrive 05:00 to 22:50 to 7 Chicago airports. Average flight time is 2h 58m.

The fastest flight 2h 45m
Average flight time 2h 58m
The earliest flight 05:00
The latest flight 22:50
Distance 852 ml

The cheapest months to travel to Chicago are november (from 56 $), december (from 56 $), january (from 62 $).

The most expensive months are february (from 67 $), january (from 62 $), december (from 56 $).

What is the lowest airfare Boston to Chicago?

The cheapest plane ticket found by our users is $56. This airfare is for economy class on one-way NK1988 flight by Spirit Airlines for December 10, 2024 which leaves Logan in Boston at 10:34 am and arrives at Chicago O'Hare International at 21:07.

Economy class

$56

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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 15 regular airlines and 6 low-cost airlines. Most of the flights on this route are operated by American Airlines - 96 departures per week at the price of from $ 67 . And the most expensive tickets are offered by Austrian Airlines airline - from $ 6303.

Direct flights

There are 30 nonstop flights on the route. The fastest direct flight is WN787 by Southwest Airlines takes 2h 45m and the cheapest is NK1988 by Spirit Airlines for $57.

AA - American Airlines

from $67

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B6 - JetBlue

from $57

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WN - Southwest Airlines

from $78

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DL - Delta Air Lines Inc.

from $75

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UA - United Airlines

from $63

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NK - Spirit Airlines

from $72

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See more direct flights

Connecting Flights

There are 545 flights with layovers on the route. The fastest connecting flight is DL1019 by Delta Air Lines Inc. takes 4h 30m and the cheapest is NK1988 by Spirit Airlines for $56.

AA - American Airlines

from $96

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DL - Delta Air Lines Inc.

from $120

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UA - United Airlines

from $97

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AS - Alaska Airlines

from $215

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B6 - JetBlue

from $75

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PD - Porter Airlines

from $277

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NK - Spirit Airlines

from $56

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EI - Aer Lingus

from $1216

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OS - Austrian Airlines

from $6303

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LX - SWISS International Air Lines

from $5946

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F9 - Frontier Airlines

from $56

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TK - Turkish Airlines

from $1910

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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 $56
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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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Airplanes

There are flights to Chicago from Boston by 15 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Embraer Lineage 1000

from $57

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Boeing 737-800

from $67

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Embraer 175 (short wing)

from $67

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Airbus A320

from $75

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Embraer 170

from $120

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Boeing 737-900

from $153

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Airbus A321

from $153

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Boeing 757-200

from $154

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Airbus A319

from $154

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Boeing 757

from $168

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Top Domestic Destinations from Boston

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

Boston — Orlando

from $67

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Boston — Newark

from $73

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Boston — Minneapolis

from $54

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Boston — Chicago

from $59

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Boston — Los Angeles

from $62

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Boston — Las Vegas

from $63

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Boston — San Francisco

from $61

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Boston — New York

from $57

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Boston — Miami

from $56

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Boston — Louisville

from $69

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Top International Destinations from Boston

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.

Boston — Rome

from $77

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Boston — London

from $76

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Boston — Zurich

from $68

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Boston — Paris

from $76

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Boston — Manchester

from $68

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Boston — Dublin

from $54

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Boston — Athens

from $59

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Boston — Lisbon

from $66

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Boston — Barcelona

from $67

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Boston — Munich

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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