Cheap Flights from Boston, MA to Chicago, IL from $62

One way Round trip

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On Cheapflightsplus.com you will find 7 direct and 105 connecting flights from Boston to Chicago. You can compare airfare deals from 7 airlines and multiple travel sites from $62, 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: $62 (one-way), $106 (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 $62. The fastest direct flight takes 2h 56m and the fastest connecting – 4h 59m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $122 Find flight	09:30 Boston Logan	11:28 Chicago O'Hare International	2h 58m	United Airlines	UA216
from $122 Find flight	10:57 Boston Logan	12:55 Chicago O'Hare International	2h 58m	United Airlines	UA267
from $122 Find flight	12:12 Boston Logan	14:10 Chicago O'Hare International	2h 58m	United Airlines	UA222
from $124 Find flight	09:20 Boston Logan	11:22 Chicago O'Hare International	3h 2m	United Airlines	UA260
from $242 Find flight	18:25 Boston Logan	20:25 Chicago O'Hare International	3h 0m	United Airlines	UA1015
from $62 Find flight	11:26 Boston Logan	20:13 Chicago O'Hare International	9h 47m layover 2h 47m - Miami	Spirit Airlines	NK2975 NK19
from $67 Find flight	11:35 Boston Logan	22:41 Chicago Midway	12h 6m layover 5h 42m - Dallas	Frontier Airlines	F93601 F92882
from $70 Find flight	11:05 Boston Logan	18:48 Chicago Midway	8h 43m layover 2h 31m - Tampa	Frontier Airlines	F91215 F91185
from $81 Find flight	06:00 Boston Logan	10:55 Chicago Midway	5h 55m layover 1h 13m - Atlanta	Frontier Airlines	F93511 F92143
from $81 Find flight	12:36 Boston Logan	19:13 Chicago Midway	7h 37m layover 3h 52m - Philadelphia	Frontier Airlines	F93011 F94367
from $81 Find flight	11:07 Boston Logan	19:18 Chicago Midway	9h 11m layover 2h 16m - Miami	Frontier Airlines	F91435 F92109
from $87 Find flight	09:16 Boston Logan	21:55 Chicago Midway	13h 39m layover 9h 36m - Raleigh	Frontier Airlines	F93057 F93717
from $87 Find flight	06:00 Boston Logan	23:16 Chicago O'Hare International	18h 16m layover 11h 29m - Orlando	Frontier Airlines	F91977 F93045
from $91 Find flight	09:00 Boston Logan	18:42 Chicago O'Hare International	10h 42m layover 6h 14m - Charlotte	Frontier Airlines	F93613 F93141
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 December 21, 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
09:20 — 11:22	09:20 — 11:22 UA260 United Airlines Boston — Chicago	3h 2m	Find flight from$124
09:30 — 11:28	09:30 — 11:28 UA216 United Airlines Boston — Chicago	2h 58m	Find flight from$122
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
12:12 — 14:10	12:12 — 14:10 UA222 United Airlines Boston — Chicago	2h 58m	Find flight from$122
18:25 — 20:25	18:25 — 20:25 UA1015 United Airlines Boston — Chicago	3h	Find flight from$242
19:59 — 21:55	19:59 — 21:55 UA1783 United Airlines Boston — Chicago	2h 56m	Find flight from$139
05:45 — 09:44	05:45 — 07:31 UA1734 United Airlines Boston — Washington D.C. 54m stop 08:25 — 09:44 UA2440 United Airlines Washington D.C. — Chicago	4h 59m including layover	Find flight from$132
05:45 — 14:32	05:45 — 09:20 NK867 Spirit Airlines Boston — Miami 2h 50m stop 12:10 — 14:32 NK3934 Spirit Airlines Miami — Chicago	9h 47m including layover	Find flight from$173
06:00 — 16:08	06:00 — 09:32 NK2990 Spirit Airlines Boston — Orlando 4h 25m stop 13:57 — 16:08 NK223 Spirit Airlines Orlando — Chicago	11h 8m including layover	Find flight from$62
06:00 — 10:55	06:00 — 09:08 F93511 Frontier Airlines Boston — Atlanta 1h 13m stop 16:18 — 17:18 F92143 Frontier Airlines Atlanta — Chicago	5h 55m including layover	Find flight from$81
07:10 — 13:10	07:10 — 08:38 UA570 United Airlines Boston — Newark 2h 54m stop 11:32 — 13:10 UA510 United Airlines Newark — Chicago	7h including layover	Find flight from$132
07:10 — 11:38	07:30 — 08:58 UA570 United Airlines Boston — Newark 1h 23m stop 10:30 — 12:04 UA1525 United Airlines Newark — Chicago	5h 28m including layover	Find flight from$133
08:36 — 14:40	08:36 — 10:00 UA515 United Airlines Boston — Newark 2h 58m stop 12:58 — 14:40 UA1946 United Airlines Newark — Chicago	7h 4m including layover	Find flight from$182
09:00 — 18:42	08:57 — 11:27 F93613 Frontier Airlines Boston — Charlotte 6h 14m stop 21:35 — 22:57 F93141 Frontier Airlines Charlotte — Chicago	10h 42m including layover	Find flight from$91
09:16 — 21:55	09:16 — 11:18 F93057 Frontier Airlines Boston — Raleigh 9h 36m stop 20:54 — 21:55 F93717 Frontier Airlines Raleigh — Chicago	13h 39m including layover	Find flight from$87
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
11:26 — 22:51	11:26 — 15:03 NK2975 Spirit Airlines Boston — Miami 5h 27m stop 20:30 — 22:51 NK718 Spirit Airlines Miami — Chicago	12h 25m including layover	Find flight from$62
12:36 — 19:13	12:36 — 14:08 F93011 Frontier Airlines Boston — Philadelphia 3h 52m stop 18:00 — 19:13 F94367 Frontier Airlines Philadelphia — Chicago	7h 37m including layover	Find flight from$81
13:53 — 22:51	13:53 — 17:30 NK370 Spirit Airlines Boston — Miami 3h stop 20:30 — 22:51 NK718 Spirit Airlines Miami — Chicago	9h 58m including layover	Find flight from$133
14:00 — 22:57	13:53 — 15:30 UA2454 United Airlines Boston — Newark 6h stop 21:29 — 23:00 UA1308 United Airlines Newark — Chicago	9h 57m including layover	Find flight from$212
14:45 — 18:55	14:45 — 16:28 UA214 United Airlines Boston — Washington D.C. 1h 8m stop 17:36 — 18:55 UA1117 United Airlines Washington D.C. — Chicago	5h 10m including layover	Find flight from$132
17:50 — 22:57	17:25 — 19:00 UA1606 United Airlines Boston — Newark 2h 9m stop 21:29 — 23:00 UA1308 United Airlines Newark — Chicago	6h 7m including layover	Find flight from$132
18:55 — 22:57	18:55 — 20:30 UA521 United Airlines Boston — Newark 1h stop 21:29 — 23:00 UA1308 United Airlines Newark — Chicago	5h 2m including layover	Find flight from$133
19:24 — 07:18 +1 day	19:24 — 22:55 NK870 Spirit Airlines Boston — Orlando 6h 15m stop 05:10 — 07:18 NK1683 Spirit Airlines Orlando — Chicago	12h 54m including layover	Find flight from$133
15:15 — 01:13 +1 day	15:15 — 17:15 NK2328 Spirit Airlines Boston — Detroit 1h 27m stop 18:42 — 20:32 NK1020 Spirit Airlines Detroit — Dallas 2h 27m stop 22:59 — 01:13 NK828 Spirit Airlines Dallas — Chicago	10h 58m including layover	Find flight from$183
16:25 — 09:52 +1 day	16:25 — 19:35 NK1363 Spirit Airlines Boston — Atlanta 2h 17m stop 21:52 — 23:48 NK501 Spirit Airlines Atlanta — Miami 7h 42m stop 07:30 — 09:52 NK1986 Spirit Airlines Miami — Chicago	18h 27m including layover	Find flight from$102

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

*Departure and arrival times - local. Updated on December 21, 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 05:45 to 21:55 from 4 Boston airports and arrive 05:45 to 21:55 to 7 Chicago airports. Average flight time is 2h 58m.

The fastest flight 2h 56m
Average flight time 2h 58m
The earliest flight 05:45
The latest flight 21:55
Distance 852 ml

The cheapest months to travel to Chicago are december (from 59 $), january (from 62 $), november (from 64 $).

The most expensive months are february (from 67 $), november (from 64 $), january (from 62 $).

What is the lowest airfare Boston to Chicago?

The cheapest plane ticket found by our users is $62. This airfare is for economy class on one-way NK2975 flight by Spirit Airlines for January 22, 2025 which leaves Logan in Boston at 11:26 am and arrives at Chicago O'Hare International at 22:51.

Economy class

$62

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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 7 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Porter Airlines - 1 departures per week at the price of from $ 317 . And the most expensive tickets are offered by Austrian Airlines airline - from $ 6303.

Direct flights

There are 7 nonstop flights on the route. The fastest direct flight is UA1783 by United Airlines takes 2h 56m and the cheapest is NK2975 by Spirit Airlines for $122.

UA - United Airlines

from $122

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Connecting Flights

There are 105 flights with layovers on the route. The fastest connecting flight is UA1734 by United Airlines takes 4h 59m and the cheapest is NK2975 by Spirit Airlines for $62.

PD - Porter Airlines

from $317

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UA - United Airlines

from $132

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NK - Spirit Airlines

from $62

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F9 - Frontier Airlines

from $67

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OS - Austrian Airlines

from $6303

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LX - SWISS International Air Lines

from $6019

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TS - Air Transat

from $338

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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 $62
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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 7 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737-900

from $139

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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.
To find a plane ticket, please select dates.