Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Boston to Chicago

1 adult
0 bags
'This year, momondo is the #1 place for airfares on the internet.'
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customise your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Boston to Chicago

Cheap return flights

These are some of the best return flight deals from Boston to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Boston to Chicago.

Cheap last-minute flights

Planning a quick getaway from Boston to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from Boston to Chicago

Find recent round-trip train or bus tickets from Boston to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
BOS-ORD
2h 59mdirect
ORD-BOS
2h 16mdirect
Japan Airlines
Find Deal
BOS-ORD
2h 54mdirect
ORD-BOS
2h 15mdirect
Icelandair
Find Deal
BOS-ORD
3h 01mdirect
ORD-BOS
2h 26mdirect
BOS-ORD
3h 03mdirect
ORD-BOS
2h 23mdirect
Air New Zealand
Find Deal
BOS-ORD
3h 03mdirect
ORD-BOS
2h 23mdirect
United Airlines
Find Deal
BOS-ORD
3h 10mdirect
ORD-BOS
2h 26mdirect
BOS-MDW
2h 50mdirect
MDW-BOS
2h 10mdirect
Southwest
Find Deal
BOS-ORD
3h 10mdirect
ORD-BOS
2h 28mdirect
Scandinavian Airlines
Find Deal
BOS-ORD
3h 03mdirect
ORD-BOS
2h 21mdirect
Iberia
Find Deal
BOS-ORD
2h 59mdirect
ORD-BOS
2h 28mdirect
Korean Air
Find Deal
BOS-ORD
3h 01mdirect
ORD-BOS
2h 42mdirect
WestJet
Find Deal
BOS-ORD
2h 59mdirect
ORD-BOS
2h 33mdirect
American Airlines
Find Deal
BOS-ORD
3h 06mdirect
ORD-BOS
2h 24mdirect
BOS-ORD
3h 07mdirect
ORD-BOS
2h 18mdirect
Qatar Airways
Find Deal
BOS-ORD
2h 47mdirect
ORD-BOS
2h 24mdirect
Emirates
Find Deal
BOS-ORD
3h 04mdirect
ORD-BOS
2h 33mdirect
Alaska Airlines
Find Deal
BOS-ORD
3h 07mdirect
ORD-BOS
2h 15mdirect
JetBlue
Find Deal
BOS-ORD
3h 04mdirect
ORD-BOS
2h 18mdirect
Etihad Airways
Find Deal
BOS-ORD
3h 03mdirect
ORD-BOS
2h 22mdirect
Avianca
Find Deal
BOS-ORD
3h 05mdirect
ORD-BOS
2h 25mdirect
Cathay Pacific
Find Deal
BOS-ORD
3h 08mdirect
ORD-BOS
2h 30mdirect
Royal Jordanian
Find Deal
BOS-ORD
2h 52mdirect
ORD-BOS
2h 18mdirect
Hawaiian Airlines
Find Deal
BOS-ORD
3h 03mdirect
ORD-BOS
2h 23mdirect
BOS-ORD
3h 07mdirect
ORD-BOS
2h 18mdirect
TAP AIR PORTUGAL
Find Deal
BOS-ORD
2h 55mdirect
ORD-BOS
2h 26mdirect
Virgin Atlantic
Find Deal
BOS-ORD
3h 02mdirect
ORD-BOS
2h 19mdirect
British Airways
Find Deal
BOS-ORD
2h 59mdirect
Japan Airlines
Find Deal
BOS-ORD
2h 54mdirect
Icelandair
Find Deal
BOS-ORD
3h 01mdirect
BOS-ORD
3h 03mdirect
Air New Zealand
Find Deal
BOS-ORD
3h 04mdirect
United Airlines
Find Deal
BOS-ORD
3h 06mdirect
BOS-MDW
2h 50mdirect
Southwest
Find Deal
BOS-ORD
3h 10mdirect
Scandinavian Airlines
Find Deal
BOS-ORD
3h 10mdirect
Iberia
Find Deal
BOS-ORD
2h 59mdirect
Korean Air
Find Deal
BOS-ORD
3h 01mdirect
WestJet
Find Deal
BOS-ORD
2h 59mdirect
American Airlines
Find Deal
BOS-ORD
3h 00mdirect
BOS-ORD
3h 07mdirect
Qatar Airways
Find Deal
BOS-ORD
2h 47mdirect
Emirates
Find Deal
BOS-ORD
3h 04mdirect
Alaska Airlines
Find Deal
BOS-ORD
3h 07mdirect
JetBlue
Find Deal
BOS-ORD
3h 08mdirect
Etihad Airways
Find Deal
BOS-ORD
3h 03mdirect
Avianca
Find Deal
BOS-ORD
3h 04mdirect
Cathay Pacific
Find Deal
BOS-ORD
3h 03mdirect
LATAM Airlines
Find Deal
BOS-ORD
3h 08mdirect
Royal Jordanian
Find Deal
BOS-ORD
2h 54mdirect
Hawaiian Airlines
Find Deal
BOS-ORD
3h 03mdirect
BOS-ORD
2h 54mdirect
TAP AIR PORTUGAL
Find Deal
BOS-ORD
2h 55mdirect
Virgin Atlantic
Find Deal
BOS-ORD
3h 02mdirect
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 422.

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?

The best time to book a flight to Chicago from Boston is 57 days out, which is when prices tend to be around R4 464. However, in the past 72 hours, people saw flights from Boston for as low as R55 927.

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 December 2024, prices for Boston to Chicago flights are approximately 0% more expensive 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.


An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Fri 27/12
Fri 3/1
Email me momondo's favourite deals

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