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The above chart lists Chicago to Boston flights with the US and non-US based airlines. The airfares against flights from Chicago to Boston are based on a recent trend. The fares are likely to change. The airfare comprises of base fare, fuel surcharges, airline/airport taxes, and our service fee.

Search, Compare and Book Flights from Chicago to Boston

Empowering you with the world’s best travel technology, Cheapfaremart allows you to compare fares for Chicago to Boston bound flights with budget as well as full-service airlines.

Customize the flight search by the economy, premium economy, business, or first class. Sorting of flight options by departure and arrival timing and airlines is also possible.

Staying true to our commitment to offering cheap flights from Chicago to Boston, we have introduced Price Match Satisfaction (PMS) policy. Within 24 hours of your air ticket purchase at Cheapfaremart, if you come across the same travel itinerary with any significant travel agents in the US at a lower price, we will refund the difference in fare, provided you submit to us verifiable sources. On your sole discretion, you may also go for ticket cancellation free of cost.

Airports in Chicago

O’Hare International Airport

O’Hare International Airport (IATA: ORD, ICAO: KORD) is located 14 miles (23 km) northwest of the Loop business district. The airport handles flights to 228 destinations in North America, South America, Europe, Africa, Asia, and Oceania.

The airport is a focus city for Frontier Airlines and Spirit Airlines, which are renowned ultra-low cost and low-cost airlines in the world.

Chicago Midway International Airport

Located eight miles (13 km) from the Loop, Chicago Midway International Airport (IATA: MDW, ICAO: KMDW) is on the southwest side of Chicago. Until the opening of O’Hare International Airport in 1955. Today, Midway is the second-largest airport in Chicago metropolitan area and the state of Illinois, serving 22,027,737 passengers in 2018. The airport is a focus city for Southwest Airlines.

Airports in Boston

Logan International Airport

Boston Logan International Airport (IATA: BOS, ICAO: KBOS) and simply Logan Airport is 4 miles from the center of Boston, MA. It’s an international airport in the East Boston neighborhood of Boston, Massachusetts. A record 40,941,925 passengers enplaned and deplaned at the airport in 2017 thereby making the airport the 16th-busiest airport in the United States.  The airport is named after General Edward Lawrence Logan, a war hero native to Boston. Logan Airport has flight services to destinations across the United States, Canada, Mexico, Latin America, the Caribbean, the North Atlantic region (including Bermuda and the Azores), Europe, and Asia. Check the fares for flights from ORD to BOS or perform a new search.

Nonstop Flights from Chicago to Boston

Looking for the shortest flight route from Chicago to Boston? Take a look at the nonstop flight choices you have with different departure-arrival pairs. 



Flights from ORD to BOS

JetBlue, Delta Connection, United Airlines, and American Airlines, Spirit, Frontier Airlines

Flight from MDW to BOS

No Airlines

How Long is the Flight from Chicago to Boston?

Are you to board a flight to Boston from Chicago for the first time? If yes, you would be interested in knowing the flight time and flight distance between the two cities.


Flight Distance

Flight Time

Flights from ORD to BOS

866 miles/1394 km

2 hours 39 minutes

Flight from MDW to BOS

860 miles/1385 km

2 hour, 35 minutes

Note: The aircraft speed is assumed to be 500 miles per hour or 804.67 km per hour.

How to Book Cheap Flights from Chicago to Boston?

1. Be flexible with airlines

Wish to travel in comfort and luxury or just with some basic amenities?  The choice remains with you. From full-service to low-cost to ultra-low-cost – all types of suppliers are available on Chicago to Boston flight route.  Compare fares and lock your cheap flights from Chicago to Boston.

2. Be flexible with travel days

Weekend vs. Weekday flights. Most of the cheap flight deals from Boston to Chicago are available in the weekdays only. Hence, if you are flexible with your days, the trick would help you save big on your Chicago airline ticket purchase.

3. Be flexible with the travel dates

It’s our job to help you find the cheapest flight ticket, and our Flexible Date Fare recommendation takes it a step ahead. You will notice a significant difference between the regular fare and flexible fare. If the dates are adjustable, confirm your air reservation with a flexible date fare.

4. Go in low-season

Summer, from June to August, is the cheapest season to fly in Boston. Most of the travelers avoid the season due to the hot and humid weather. The average temperature stays around 90s degree Fahrenheit. To make good of the low demand for flights, suppliers often drop their fares by offering discounted airfare to Boston.

5. Fly with budget airlines

With Spirit and Frontier operating on this route, you are in for a great flight deal. Even if it’s about making your way through a flagship airline like American or United, Cheapfaremart has got you covered with the best airfare deals. However, we recommend you to take note of the fine-print regarding the economy and basic economy fares. The latter is highly restricted. Such a flight ticket is usually non-refundable. Also, there is no upgrade available if you want to make.

6. Frequently Asked Questions

If you think we didn’t answer your question, tour our FAQs page where we have tried to answer most of the questions regarding flight ticket purchases, cancellation, refund, airport screening, travel documents, and other aspects of your flight to Boston.

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