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Cheap flights from Chicago to Boston

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Cheap return flights

KAYAK's recommended return flight deals from the most popular airlines that fly from Chicago to Boston.
ORD-BOS
2h 24mdirect
BOS-ORD
3h 00mdirect
Japan Airlines
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ORD-BOS
2h 25mdirect
BOS-ORD
2h 52mdirect
Icelandair
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ORD-BOS
2h 28mdirect
BOS-ORD
2h 57mdirect
ORD-BOS
2h 26mdirect
BOS-ORD
2h 58mdirect
Air New Zealand
Find Deal
ORD-BOS
2h 26mdirect
BOS-ORD
2h 58mdirect
United Airlines
Find Deal
ORD-BOS
2h 28mdirect
BOS-ORD
2h 54mdirect
MDW-BOS
2h 10mdirect
BOS-MDW
2h 35mdirect
Southwest
Find Deal
ORD-BOS
2h 28mdirect
BOS-ORD
3h 00mdirect
Scandinavian Airlines
Find Deal
ORD-BOS
2h 25mdirect
BOS-ORD
2h 55mdirect
Iberia
Find Deal
ORD-BOS
2h 28mdirect
BOS-ORD
2h 57mdirect
Korean Air
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ORD-BOS
2h 30mdirect
BOS-ORD
2h 59mdirect
WestJet
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ORD-BOS
2h 24mdirect
BOS-ORD
2h 55mdirect
American Airlines
Find Deal
ORD-BOS
2h 25mdirect
BOS-ORD
2h 59mdirect
ORD-BOS
2h 24mdirect
BOS-ORD
2h 52mdirect
Qatar Airways
Find Deal
ORD-BOS
2h 32mdirect
BOS-ORD
2h 57mdirect
Emirates
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ORD-BOS
2h 24mdirect
BOS-ORD
2h 54mdirect
Alaska Airlines
Find Deal
ORD-BOS
2h 25mdirect
BOS-ORD
3h 03mdirect
JetBlue
Find Deal
ORD-BOS
2h 24mdirect
BOS-ORD
3h 10mdirect
Etihad Airways
Find Deal
ORD-BOS
2h 30mdirect
BOS-ORD
2h 51mdirect
Avianca
Find Deal
ORD-BOS
2h 21mdirect
BOS-ORD
3h 02mdirect
Cathay Pacific
Find Deal
ORD-BOS
2h 24mdirect
BOS-ORD
2h 56mdirect
Royal Jordanian
Find Deal
ORD-BOS
2h 25mdirect
BOS-ORD
2h 54mdirect
Hawaiian Airlines
Find Deal
ORD-BOS
2h 28mdirect
BOS-ORD
2h 57mdirect
ORD-BOS
2h 34mdirect
BOS-ORD
3h 05mdirect
TAP AIR PORTUGAL
Find Deal
ORD-BOS
2h 25mdirect
BOS-ORD
2h 57mdirect
Virgin Atlantic
Find Deal
ORD-BOS
2h 28mdirect
BOS-ORD
3h 00mdirect
British Airways
Find Deal

See travel insights to Boston from

How to get the cheapest flight ticket from Chicago to Boston

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 Boston?

In general, September is the cheapest month to fly from Chicago to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around R3 482. If you aren’t able to travel during the month of September, then book flights to Boston from Chicago during August instead. Flights to Boston in August, while not as cheap as those in September, still average around R3 792.

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

You are more likely to see cheaper flights to Boston from Chicago when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Boston for around R4 441 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as R3 683 on momondo.

How have Chicago to Boston flight prices changed over time?

As of March 2025, prices for Chicago to Boston flights are approximately 32% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Boston

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

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

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

Direct flights

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

  • How far is Chicago to Boston Logan Intl by plane?

    The straight-line distance from Chicago to Boston Logan Intl is 1364,5 km.

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

    Prices for flights from Chicago to Boston Logan Intl Airport are updated daily.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and stopovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Boston Logan Intl Airport.

  • What documentation or ID do you need to fly to Boston Logan Intl Airport?

    The necessary travel and health documents for your Boston Logan Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's licence and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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


Travelling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Leominster
Cambridge
Salem
Brookline

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Boston. momondo saves you time and could save you money on your trip.

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

All flight searches from Chicago to Boston on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search for Chicago to Boston flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Boston from Chicago 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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