Cheap Flights from Boston Logan International to Chicago in 2019

Top last minute flight deals

Feeling spontaneous? It’s never too late to book a trip. Here’s our pick of the best last minute flights to Chicago...
Estimated lowest prices only. Found in the last 14 days.

Flight information Boston Logan International to Chicago

Cheapest roundtrip price last month


Non-stop airlines


Flights per week


Average flight time, total distance 879 miles

2h 36min

Most popular airline last month

American Airlines

Chicago O'Hare International, Chicago Midway and Chicago Rockford

3 airports

Frequently asked questions

There are 3 airports in Chicago: Chicago O'Hare International, Chicago Midway and Chicago Rockford.
The best price found on Skyscanner for a flight from Boston Logan International to Chicago is $75. This was found by aggregating across different carriers and is the cheapest price for the whole month.
2h 36min is the average flight time from Boston Logan International to Chicago.
There are 6 airlines who fly non-stop from Boston Logan International to Chicago.
There are 177 flights per week flying from Boston Logan International to Chicago, as of October.

 “The Hub” as it is known by locals, has one of the largest metropolitan areas in the United States, and is the capital of Massachusetts. Numerous major, Fortune 500 companies are headquartered in Boston, including EMC Insurance, Staples, and Raytheon. For all of these reasons, it is considered a Gamma World City, making it comparable to the destination city.

Flights from Boston to Chicago generally take 2 hours and 35 minutes; the total gate-to-gate distance is 835 miles. There are multiple airports passengers can for their arrival: O’Hare, FSS, Gary Regional, Midway, and Rockford. Five carriers offer direct routes between the two cities, including American Airlines, Continental Airlines, United Airlines, US Airways, and Alaska Airlines.

Bye-Bye, Boston

Located in the city’s eastside, Logan International is Boston’s and greater New England’s principal airport. Approximately 33 million foreign and domestic passengers traveled through its terminal in 2014, and this figure is predicted to rise in the coming years.

Every major U.S. airline company offers flights from Logan International. In addition, many well-known international carriers use the airport as a chief flight hub, especially Aer Lingus. New routes by Turkish Airlines, Cathay Pacific, Emirates, and many other foreign airliners have opened here, which is the primary reason for its high projected growth.

Four terminals and 103 passenger gates comprise Boston’s international airport; each terminal is connected to moving walkways and pre-security shuttle buses. If you are in the mood for some good food while waiting for your departure, do not miss the MooBella Ice Creamery Machine, one of Logan International’s most famous amenities. This touch-screen, ice cream machine gives customers 96 flavor choices!

Visiting Chicago: Your Itinerary At Its Finest

Baseball fans flock in droves to see the Cubs play at Wrigley Field. Shoppers cannot get enough of the city’s downtown districts. Art lovers swoon over the one-of-a-kind commercial architecture that only Chicago can claim.

Chi-Town is a whole lot of fun for anyone. Downtown is where you will find all of the major theaters, parks, museums, and stores. The Far Northwest Side is home to many incredible, historic buildings, and the Far North is the go-to place for the beach. Notable Chicago attractions include Grant Park, Music Box, Navy Pier, and The Peggy Notebaert Nature Museum.

Skyscanner wants you to remember your vacation to The Windy City for years to come. We invite you to search cheap flights from Boston to Chicago with our online Intellisearch tool. Care to save big on airfare?!

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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.