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The table displays fares for flights from Boston to Chicago with multiple carriers. The cost of every plane ticket to Chicago from Boston is based on a recent trend. Fares are non-warranted and subject to change. Fares comprise base fare, fuel surcharges, airline/airport taxes, and our service fee. Booking policy details available with Terms and Conditions.

Search, Compare and Book Flights from Boston to Chicago

Cheapfaremart maximizes your savings on the purchase of flight tickets from Boston to Chicago. We are an ARC-verified travel agency based in Orlando, Florida. Compare Boston to Chicago flight ticket cost under economy, premium economy, business or first class and confirm your tickets from Boston to Chicago today.

We empower you with technology. Customize your flight search by one-way and round-trip to get relevant airfares and plan your Chicago vacation. Our Price Match Satisfaction (PMS) policy gives you a control on your savings. Within 24 hours of your air ticket purchase with us, if you find the same travel itinerary with any major travel agents in the US at a lower price, we are ready to refund, provided you submit to us verifiable sources.

Airports in Boston

Logan International Airport

Boston Logan International Airport (IATA: BOS, ICAO: KBOS) and simply Logan Airport, is an international airport in the East Boston neighborhood of Boston, Massachusetts.

By passenger traffic stats in 2017, the airport was rated as the 16th-busiest airport in the United States. A record 40,941,925 passengers enplaned and deplaned the airport. The airport has been 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.

The airport is a focus city for Delta Air Lines and JetBlue Airways. Use our booking engine to know get a list of flights from BOS to ORD.

Airports in Chicago

O’Hare International Airport

O’Hare International Airport (IATA: ORD, ICAO: KORD), also referred to as O’Hare Airport, Chicago O’Hare, or simply O’Hare, is an international airport located on the far Northwest Side of Chicago, Illinois. The airport is 14 miles (23 km) northwest of the Loop business district. O’Hare connects Chicago with 228 destinations in North America, South America, Europe, Africa, Asia and Oceania.

The airport is a focus city for Frontier Airlines and Spirit Airlines.

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.

Nonstop Flights from Boston to Chicago

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



Flights from BOS to ORD

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

Flight from BOS to MDW

No Airlines

How Long is the Flight to Chicago from Boston?

If this is your maiden flight from Boston to Chicago, this is question that most likely to resonate your mind. The distance and time between the departure and arrival airport pair is mentioned for your reference.


Flight Distance

Flight Time

Flights from BOS to ORD

866 miles/1394 km

2 hours 39 minutes

Flight from BOS to MDW

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 Boston to Chicago?

1. Be flexible with airlines

The flight route has got several airlines from flagship carriers to the world’s leading budget carriers. Perform the flight search by your travel dates and compare the fares, fare rules and travel itinerary wisely to get the cheapest yet best flights from Boston to Chicago.

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 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 regular fare and flexible fare. If the dates are adjustable, confirm your air reservation with a flexible date fare.

4. Go in low-season

Winter, from December to February, is the cheapest season to fly in Boston. Excluding the festival or event time like Thanksgiving, Christmas and New Year, the rest of the time gives you an opportunity to find the lowest fare from BOS to ORD.

5. Fly with budget airlines

The leading low-cost carriers including Spirit and Frontier are operating on the route to help you travel to more places without getting bankrupt. The airlines offer economy fares only, carry-on baggage is chargeable. Fares are non-refundable. Also, you pay for any ticket changes.

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