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Cheap flights from Boston to Chicago from R4 083

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BOS
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CHI
2203 kmmulti-stop
Multiple Airlines Logo
CHI
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BOS
2203 kmmulti-stop
Multiple Airlines

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How to get the cheapest flight ticket from Boston to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Boston, with most prices found around R3 155. If you are unable to visit Chicago during the month of September, then departing from Boston during the month January is also very affordable. Most momondo users find prices during this month for around R3 358.

What is the cheapest day to depart on your flight to Chicago?

On average, the least expensive day to fly to Chicago from Boston is on a Friday. momondo users have found tickets for Friday departures for as low as R26 382. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Saturday is R28 109.

What is the cheapest Boston Logan Intl to Chicago flight route?

Fly from Boston Logan Intl to Chicago Midway for the best Boston Logan Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around R4 225 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Boston for as low as R3 493 on momondo.

What cabin class options are available on Boston Logan Intl to Chicago flights?

There is only 1 cabin class available to choose from on Boston Logan Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Boston to Chicago flight prices changed over time?

As of December 2025, prices for Boston to Chicago flights are approximately 21% cheaper when compared to flights at the same time last year.

When to book flights from Boston to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Boston to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Boston to Chicago (BOS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago

Best price found

R18 908

Direct flights

None
The best one-way flight to Chicago from Boston in the past 72 hours is R18 908. The best return flight deal from Boston to Chicago found on momondo in the last 72 hours is R28 109.
There are no direct flights from Boston to Chicago. Popular non-direct route for this connection is Boston Logan Intl Airport - Chicago O'Hare Intl Airport.
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  • How far is Boston Logan Intl to Chicago by plane?

    The distance between Boston Logan Intl and Chicago is about 1364,5 km.

  • When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago?

    Prices for flights from Boston Logan Intl Airport to Chicago are refreshed on a daily basis.

  • How old do you have to be to fly from Boston Logan Intl Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Boston Logan Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's licence and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Boston to Chicago?

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond

Why use momondo?

Why should I use momondo to find a flight deal from Boston to Chicago?

Finding the right flight to Chicago from Boston is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Boston to Chicago with flexible booking policies on momondo?

Flights from Boston to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Boston to Chicago?

momondo helps you find the best flight between Boston and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Boston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport