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Cheap flights from Boston to Chicago from ₹ 5,826

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Chicago departing on 31/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap return flights

Southwest Logo
05:35 - 16:25BOS-ORD
11h 50m2 stops
Southwest Logo
14:50 - 23:25ORD-BOS
7h 35m1 stop
₹ 11,035Southwest
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Sat, 25 Oct - Mon, 27 Oct
JetBlue Logo
07:09 - 09:22BOS-ORD
3h 13mdirect
JetBlue Logo
19:13 - 22:46ORD-BOS
2h 33mdirect
₹ 11,211JetBlue
Find Deal
Fri, 10 Oct - Mon, 13 Oct
United Airlines Logo
06:00 - 07:56BOS-ORD
2h 56mdirect
United Airlines Logo
06:15 - 09:30ORD-BOS
2h 15mdirect
₹ 11,388United Airlines
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Thu, 16 Oct - Sun, 9 Nov
JetBlue Logo
07:00 - 08:56BOS-ORD
2h 56mdirect
JetBlue Logo
09:51 - 13:20ORD-BOS
2h 29mdirect
₹ 11,652JetBlue
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Fri, 26 Sep - Wed, 1 Oct
JetBlue Logo
07:00 - 08:56BOS-ORD
2h 56mdirect
JetBlue Logo
19:50 - 23:25ORD-BOS
2h 35mdirect
₹ 11,741JetBlue
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Wed, 1 Oct - Wed, 1 Oct
United Airlines Logo
18:15 - 20:10BOS-ORD
2h 55mdirect
United Airlines Logo
06:30 - 09:57ORD-BOS
2h 27mdirect
₹ 11,829United Airlines
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Fri, 3 Oct - Sun, 5 Oct
JetBlue Logo
16:40 - 18:55BOS-ORD
3h 15mdirect
JetBlue Logo
19:13 - 22:46ORD-BOS
2h 33mdirect
₹ 11,917JetBlue
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Wed, 1 Oct - Mon, 6 Oct
Southwest Logo
05:00 - 12:45BOS-ORD
8h 45m1 stop
Southwest Logo
15:10 - 22:15ORD-BOS
6h 05m1 stop
₹ 12,006Southwest
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Sun, 26 Oct - Wed, 29 Oct
Delta Logo
12:45 - 14:39BOS-ORD
2h 54mdirect
Delta Logo
15:50 - 19:23ORD-BOS
2h 33mdirect
₹ 12,977Delta
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Wed, 15 Oct - Sat, 18 Oct
Delta Logo
07:20 - 09:22BOS-ORD
3h 02mdirect
Delta Logo
07:05 - 10:29ORD-BOS
2h 24mdirect
₹ 13,859Delta
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Thu, 30 Oct - Mon, 3 Nov

JetBlue flights from Boston to Chicago O'Hare Intl Airport

Our best JetBlue deals on Boston to Chicago O'Hare Intl Airport flight tickets
JetBlue
10 Oct
BOS07:09Boston Logan Intl
3h 13m
ORD09:22Chicago O'Hare Intl
13 Oct
ORD19:13Chicago O'Hare Intl
2h 33m
BOS22:46Boston Logan Intl
₹ 11,211
Find similar
JetBlue
26 Sept
BOS07:00Boston Logan Intl
2h 56m
ORD08:56Chicago O'Hare Intl
1 Oct
ORD09:51Chicago O'Hare Intl
2h 29m
BOS13:20Boston Logan Intl
₹ 11,652
Find similar
JetBlue
1 Oct
BOS07:00Boston Logan Intl
2h 56m
ORD08:56Chicago O'Hare Intl
1 Oct
ORD19:50Chicago O'Hare Intl
2h 35m
BOS23:25Boston Logan Intl
₹ 11,741
Find similar

United Airlines flights from Boston to Chicago O'Hare Intl Airport

Our best United Airlines deals on Boston to Chicago O'Hare Intl Airport flight tickets
United Airlines
16 Oct
BOS06:00Boston Logan Intl
2h 56m
ORD07:56Chicago O'Hare Intl
9 Nov
ORD06:15Chicago O'Hare Intl
2h 15m
BOS09:30Boston Logan Intl
₹ 11,388
Find similar
United Airlines
3 Oct
BOS18:15Boston Logan Intl
2h 55m
ORD20:10Chicago O'Hare Intl
5 Oct
ORD06:30Chicago O'Hare Intl
2h 27m
BOS09:57Boston Logan Intl
₹ 11,829
Find similar
United Airlines
25 Sept
BOS09:53Boston Logan Intl
2h 50m
ORD11:43Chicago O'Hare Intl
29 Sept
ORD07:30Chicago O'Hare Intl
2h 32m
BOS11:02Boston Logan Intl
₹ 12,094
Find similar

momondo Fare Finder

 
Customise your flight search to find flights from Boston to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 59,053 searches. Data last updated 14 September 2025.
Use the filters below to find and compare flights from Boston to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 25/10

05:35-16:25

2 stops11h 50m

Chicago O'Hare Intl

Mon 27/10

14:50-23:25

1 stop7h 35m

₹ 11,035

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/10

07:09-09:22

Nonstop3h 13m

Chicago O'Hare Intl

Mon 13/10

19:13-22:46

Nonstop2h 33m

₹ 11,211

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 16/10

06:00-07:56

Nonstop2h 56m

Chicago O'Hare Intl

Sun 9/11

06:15-09:30

Nonstop2h 15m

₹ 11,388

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 26/9

07:00-08:56

Nonstop2h 56m

Chicago O'Hare Intl

Wed 1/10

09:51-13:20

Nonstop2h 29m

₹ 11,652

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/10

07:00-08:56

Nonstop2h 56m

Chicago O'Hare Intl

Wed 1/10

19:50-23:25

Nonstop2h 35m

₹ 11,741

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 3/10

18:15-20:10

Nonstop2h 55m

Chicago O'Hare Intl

Sun 5/10

06:30-09:57

Nonstop2h 27m

₹ 11,829

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/10

16:40-18:55

Nonstop3h 15m

Chicago O'Hare Intl

Mon 6/10

19:13-22:46

Nonstop2h 33m

₹ 11,917

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 26/10

05:00-12:45

1 stop8h 45m

Chicago O'Hare Intl

Wed 29/10

15:10-22:15

1 stop6h 05m

₹ 12,006

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 15/10

12:45-14:39

Nonstop2h 54m

Chicago O'Hare Intl

Sat 18/10

15:50-19:23

Nonstop2h 33m

₹ 12,977

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 30/10

07:20-09:22

Nonstop3h 02m

Chicago O'Hare Intl

Mon 3/11

07:05-10:29

Nonstop2h 24m

₹ 13,859

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Boston to Chicago O'Hare Intl Airport

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 O'Hare Intl Airport?

The cheapest month to fly to Chicago O'Hare Intl Airport from Boston is in January. Flight prices, which tend to average around ₹ 18,715, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago O'Hare Intl Airport in January, then you should wait until September to fly from Boston, when ticket prices are also cheap, with an average price of ₹ 19,156.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as ₹ 13,004. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around ₹ 30,744. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago O'Hare Intl Airport.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the afternoon is the cheapest time of day to fly from Boston to Chicago O'Hare Intl Airport when you can find flight prices for as low as ₹ 14,032. Flying to Chicago O'Hare Intl Airport in the afternoon is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are ₹ 29,226 on average. Flights to Chicago O'Hare Intl Airport from Boston in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around ₹ 22,025 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Boston for as low as ₹ 19,156 on momondo.

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

There are 4 cabin classes available to choose from on Boston Logan Intl to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Boston to Chicago O'Hare Intl Airport flights?

You could potentially save up to 26% on your flight if you consider stops on a Boston to Chicago O'Hare Intl Airport flight.

How have Boston to Chicago O'Hare Intl Airport flight prices changed over time?

As of September 2025, prices for Boston to Chicago O'Hare Intl Airport flights are approximately 5% cheaper when compared to flights at the same time last year.

When to book flights from Boston to Chicago O'Hare Intl Airport

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

Cheap Boston to Chicago O'Hare Intl Airport (BOS to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago O'Hare Intl Airport

Best price found

₹ 7,812

Fastest flight time

2h 45m

Direct flights

Every day
The best flight deal from Boston to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is ₹ 7,812
The fastest flight from Boston to Chicago O'Hare Intl Airport takes 2h 45m
Direct flights go from Boston to Chicago O'Hare Intl Airport every day.
Search flight deals

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

    Boston Logan Intl and Chicago O'Hare Intl are 1385.7 km apart from one another. A reasonable flight in good conditions will take 2h 50m.

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

    Prices for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Boston Logan Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport 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 license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. 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 O'Hare Intl Airport?

  • What is the most popular airline from Boston to Chicago O'Hare Intl Airport?

Best airlines flying from Boston to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Boston to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom ₹ 7,812Free CancellationRating
7.9
7,956 reviews
Search Delta flights
American AirlinesPriceFrom ₹ 18,280Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • Delta Flights From Boston to Chicago O'Hare Intl Airport

    Delta is one of the most popular airlines flying from Boston to Chicago O'Hare Intl Airport, operating 12 flights/week on average for this route. A good Delta flight deal for Boston to Chicago O'Hare Intl Airport starts from ₹ 88 round-trip, up to an average price of ₹ 248. Our users have rated Delta at 7.9/10.

  • American Airlines Flights From Boston to Chicago O'Hare Intl Airport

    American Airlines (7.2/10 from 10,000 reviews) operates around 52 flights from Boston to Chicago O'Hare Intl Airport in any given week. The average American Airlines airfare for this route is around ₹ 331, with deals from around ₹ 207 rare but found on momondo. Referenced prices are for round-trip Boston to Chicago O'Hare Intl Airport flight searches in the last 72 hours.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Rosemont
Porter
Schaumburg
Oak Brook
Merrillville
Willowbrook

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Boston.

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

momondo does allow users to show only those flights to Chicago from Boston which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Boston to Chicago 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 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 O'Hare Intl Airport 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.
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