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Cheap flights from Chicago to Boston

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Find the cheapest flights from Chicago to Boston

Cheap return flights

These are some of the best return flight deals from Chicago to Boston 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 Chicago to Boston.

Cheap last-minute flights

Planning a quick getaway from Chicago to Boston? 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 Boston, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from Chicago to Boston

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

All round-trip flight deals to Boston

The cheapest plane tickets to Boston found on KAYAK recently.
ORD-BOS
2h 16mdirect
BOS-ORD
2h 59mdirect
Japan Airlines
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ORD-BOS
2h 15mdirect
BOS-ORD
2h 52mdirect
Icelandair
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ORD-BOS
2h 26mdirect
BOS-ORD
3h 01mdirect
ORD-BOS
2h 23mdirect
BOS-ORD
3h 03mdirect
Air New Zealand
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ORD-BOS
2h 23mdirect
BOS-ORD
3h 04mdirect
United Airlines
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ORD-BOS
2h 26mdirect
BOS-ORD
3h 10mdirect
MDW-BOS
2h 15mdirect
BOS-MDW
2h 50mdirect
Southwest
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ORD-BOS
2h 30mdirect
BOS-ORD
3h 10mdirect
Scandinavian Airlines
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ORD-BOS
2h 21mdirect
BOS-ORD
3h 05mdirect
Iberia
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ORD-BOS
2h 30mdirect
BOS-ORD
3h 08mdirect
Korean Air
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ORD-BOS
2h 28mdirect
BOS-ORD
2h 53mdirect
WestJet
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ORD-BOS
2h 33mdirect
BOS-ORD
2h 59mdirect
American Airlines
Find Deal
ORD-BOS
2h 20mdirect
BOS-ORD
3h 06mdirect
ORD-BOS
2h 18mdirect
BOS-ORD
3h 07mdirect
Qatar Airways
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ORD-BOS
2h 25mdirect
BOS-ORD
2h 47mdirect
Emirates
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ORD-BOS
2h 33mdirect
BOS-ORD
3h 04mdirect
Alaska Airlines
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ORD-BOS
2h 15mdirect
BOS-ORD
3h 07mdirect
JetBlue
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ORD-BOS
2h 18mdirect
BOS-ORD
3h 04mdirect
Etihad Airways
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ORD-BOS
2h 21mdirect
BOS-ORD
3h 03mdirect
Avianca
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ORD-BOS
2h 25mdirect
BOS-ORD
3h 05mdirect
Cathay Pacific
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ORD-BOS
2h 16mdirect
BOS-ORD
3h 04mdirect
Royal Jordanian
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ORD-BOS
2h 18mdirect
BOS-ORD
3h 07mdirect
Hawaiian Airlines
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ORD-BOS
2h 23mdirect
BOS-ORD
3h 04mdirect
ORD-BOS
2h 18mdirect
BOS-ORD
2h 52mdirect
TAP AIR PORTUGAL
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ORD-BOS
2h 26mdirect
BOS-ORD
2h 55mdirect
Virgin Atlantic
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ORD-BOS
2h 19mdirect
BOS-ORD
3h 02mdirect
British Airways
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ORD-BOS
2h 16mdirect
Japan Airlines
Find Deal
ORD-BOS
2h 15mdirect
Icelandair
Find Deal
ORD-BOS
2h 26mdirect
ORD-BOS
2h 23mdirect
Air New Zealand
Find Deal
ORD-BOS
2h 23mdirect
United Airlines
Find Deal
ORD-BOS
2h 26mdirect
MDW-BOS
2h 15mdirect
Southwest
Find Deal
ORD-BOS
2h 30mdirect
Scandinavian Airlines
Find Deal
ORD-BOS
2h 21mdirect
Iberia
Find Deal
ORD-BOS
2h 30mdirect
Korean Air
Find Deal
ORD-BOS
2h 28mdirect
WestJet
Find Deal
ORD-BOS
2h 33mdirect
American Airlines
Find Deal
ORD-BOS
2h 20mdirect
ORD-BOS
2h 18mdirect
Qatar Airways
Find Deal
ORD-BOS
2h 25mdirect
Emirates
Find Deal
ORD-BOS
2h 33mdirect
Alaska Airlines
Find Deal
ORD-BOS
2h 15mdirect
JetBlue
Find Deal
ORD-BOS
2h 18mdirect
Etihad Airways
Find Deal
ORD-BOS
2h 21mdirect
Avianca
Find Deal
ORD-BOS
2h 25mdirect
Cathay Pacific
Find Deal
ORD-BOS
2h 16mdirect
Royal Jordanian
Find Deal
ORD-BOS
2h 18mdirect
Hawaiian Airlines
Find Deal
ORD-BOS
2h 23mdirect
ORD-BOS
2h 18mdirect
TAP AIR PORTUGAL
Find Deal
ORD-BOS
2h 26mdirect
Virgin Atlantic
Find Deal
ORD-BOS
2h 19mdirect
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 448. If you aren’t able to travel during the month of September, then book flights to Boston from Chicago during January instead. Flights to Boston in January, while not as cheap as those in September, still average around R3 574.

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

Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago - Boston Logan Intl flight prices

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

The ideal time to book your flight to Boston is 35 days in advance, when prices tend to average R4 400. Keep in mind that you might also find cheap flights to Boston outside of this time window. In fact, momondo users recently found flights from Chicago to Boston for R57 674.

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

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

How have Chicago to Boston flight prices changed over time?

As of November 2024, prices for Chicago to Boston flights are approximately 11% cheaper 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?


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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