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Cheap flights from Boston to Chicago

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Find the cheapest flights from Boston to Chicago

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Boston to Chicago.
Japan Airlines Logo
BOS-ORD
2h 54mdirect
Japan Airlines
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Icelandair Logo
BOS-ORD
2h 55mdirect
Icelandair
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Delta Logo
BOS-ORD
2h 57mdirect
Air New Zealand Logo
BOS-ORD
2h 58mdirect
Air New Zealand
Find Deal
United Airlines Logo
BOS-ORD
2h 58mdirect
United Airlines
Find Deal
EL AL Logo
BOS-ORD
2h 54mdirect
Southwest Logo
BOS-MDW
2h 35mdirect
Southwest
Find Deal
Scandinavian Airlines Logo
BOS-ORD
2h 58mdirect
Scandinavian Airlines
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Iberia Logo
BOS-ORD
3h 01mdirect
Iberia
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Korean Air Logo
BOS-ORD
2h 57mdirect
Korean Air
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WestJet Logo
BOS-ORD
3h 00mdirect
WestJet
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American Airlines Logo
BOS-ORD
2h 58mdirect
American Airlines
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KLM Logo
BOS-ORD
2h 55mdirect
Qatar Airways Logo
BOS-ORD
2h 54mdirect
Qatar Airways
Find Deal
Emirates Logo
BOS-ORD
2h 57mdirect
Emirates
Find Deal
Alaska Airlines Logo
BOS-ORD
2h 54mdirect
Alaska Airlines
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JetBlue Logo
BOS-ORD
3h 05mdirect
JetBlue
Find Deal
Etihad Airways Logo
BOS-ORD
2h 50mdirect
Etihad Airways
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Avianca Logo
BOS-ORD
2h 51mdirect
Avianca
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Cathay Pacific Logo
BOS-ORD
3h 00mdirect
Cathay Pacific
Find Deal
LATAM Airlines Logo
BOS-ORD
2h 52mdirect
LATAM Airlines
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Royal Jordanian Logo
BOS-ORD
2h 56mdirect
Royal Jordanian
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Hawaiian Airlines Logo
BOS-ORD
2h 55mdirect
Hawaiian Airlines
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ANA Logo
BOS-ORD
2h 57mdirect
TAP AIR PORTUGAL Logo
BOS-ORD
2h 54mdirect
TAP AIR PORTUGAL
Find Deal
Spirit Airlines Logo
BOS-ORD
2h 53mdirect
Spirit Airlines
Find Deal
Virgin Atlantic Logo
BOS-ORD
2h 57mdirect
Virgin Atlantic
Find Deal
British Airways Logo
BOS-ORD
3h 00mdirect
British Airways
Find Deal

See travel insights to Chicago from

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 367. 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 628.

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

Fly from Boston Logan Intl to Chicago O'Hare Intl 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 23 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around R4 629 when searching 23 weeks out.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 703 on momondo.

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

There are 2 cabin classes 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 April 2025, prices for Boston to Chicago flights are approximately 2% 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

Direct flights

None
There are no direct flights from Boston to Chicago. There are no popular flight routes from Boston to Chicago.

  • 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?


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