Call 24/7 Toll Free
+1-855-976-5502

Compare Cheap Flights from Chicago to Boston

Search, Compare and Book

Book Flight Tickets

From
To
Departure
Return
Travelers & Class

Why Packed Bag?

icon1

Search The Most Trusted Sites

icon1

Lowest Fares Guaranteed

icon1

24/7 Support

Round Trip Flights from Chicago to Boston

06 Dec
ORD
08 Dec
BOS
$ 141.18
07 Dec
ORD
08 Dec
BOS
$ 156.94
04 Dec
ORD
10 Dec
BOS
$ 156.94
07 Dec
ORD
08 Dec
BOS
$ 156.94
30 Dec
MDW
01 Jan
BOS
$ 157.97
27 Nov
ORD
29 Nov
BOS
$ 466.24
*Note: All fares are quoted in USD.

Last updated on Wednesday 11/20/2024 at 05:00 AM, the fares mentioned above are for flight tickets and inclusive of fuel surcharges, service fee and taxes. Based on historical data, these fares are subject to change without prior notice and cannot be guaranteed at the time of booking. Kindly go through our terms and conditions before booking.

Book Chicago To Boston Flights

From the cobblestone streets to red-brick buildings, markets, and picturesque neighborhoods, Boston has a perfect blend of modernity and history. The city is blessed with a glorifying past that was the reason for many revolutions. From being home to the World’s Oldest Annual Marathon to playing an influential role in the American Revolution, the city has set milestones that still inspire and amaze people. The Freedom Trail is among the most popular places where you can explore historical places, visit museums and churches, explore the old burial grounds, and more.

The city has a rich cultural influence, and you can witness more than 450,000 works of art at the Museum of Fine Arts. This is the most popular museum exhibiting the collection from Asia, Europe, and other parts of the world. Beacon Hill in Boston is another attraction adorned by the perfect combination of Federal and Greek revival architecture. 

To witness the best of Boston, plan a vacation anytime from September through December. This is the best time to book cheap flights from Chicago to Boston. Regular flights operate between Chicago O'Hare International Airport (ORD) and Boston Logan International Airport (BOS). You can also board a flight from Chicago Midway International Airport.United Airlines, Spirit Airlines, Southwest Airlines, and Delta are among the top airlines operating CHI to BOS flights. For any inquiries regarding Chicago to Boston flights, you can call our team of experts who can assist you with flight deals, offers, and more. We are available 24/7.

Finding Cheap Flights From Chicago To Boston : Frequently Asked Questions

* The mentioned flight facts are based on the last 3 months' data. Information regarding the highest and lowest booking months is based on the last 12 months' data.

Major Carriers Operating Flights From Chicago To Boston
Airline Cheapest Average

UNITED AIRLINES $76 $294

SPIRIT AIRLINES $46 $211

AMERICAN AIRLINES $78 $293

Low Cost Carriers Operating Flights From Chicago To Boston
Airline Cheapest Average

SPIRIT AIRLINES $46 $211

FRONTIER AIRLINES $64 $362

UNITED AIRLINES $76 $294

Inspiration to Escape the Mundane

Check out exciting travel stories, travel guides and tips to inspire your next great adventure.

image
Nov 15, 2024

Delta's Centennial Celebration!

The event set to unfold on the 7th of January 2025 will be hosted by the airline?s CEO Ed Bastian who will commemorate Delta?s airline's spirit of innovation and present the blueprint of its vision of using technology to augment human experience for the coming 100 years.