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Cheap flights from Boston to Chicago from ₹ 6,150

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 18/2. 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

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United Airlines Logo
18:28 - 20:30
BOS
-
ORD
3h 02mdirect
United Airlines Logo
18:20 - 21:48
ORD
-
BOS
2h 28mdirect
₹ 12,210United Airlines
Fri, 20 Feb - Tue, 24 Feb
JetBlue Logo
07:00 - 09:10
BOS
-
ORD
3h 10mdirect
JetBlue Logo
10:00 - 13:20
ORD
-
BOS
2h 20mdirect
₹ 12,301JetBlue
Fri, 27 Feb - Mon, 2 Mar
United Airlines Logo
07:00 - 09:00
BOS
-
ORD
3h 00mdirect
United Airlines Logo
06:00 - 09:25
ORD
-
BOS
2h 25mdirect
₹ 12,391United Airlines
Fri, 3 Apr - Sun, 5 Apr
United Airlines Logo
06:00 - 08:00
BOS
-
ORD
3h 00mdirect
United Airlines Logo
21:15 - 00:35
ORD
-
BOS
2h 20mdirect
₹ 12,572United Airlines
Thu, 5 Mar - Mon, 9 Mar
United Airlines Logo
06:00 - 08:00
BOS
-
ORD
3h 00mdirect
United Airlines Logo
07:30 - 10:49
ORD
-
BOS
2h 19mdirect
₹ 12,662United Airlines
Thu, 26 Feb - Sun, 1 Mar
United Airlines Logo
06:00 - 07:59
BOS
-
ORD
2h 59mdirect
United Airlines Logo
09:15 - 12:46
ORD
-
BOS
2h 31mdirect
₹ 12,753United Airlines
Sun, 29 Mar - Wed, 1 Apr
JetBlue Logo
17:38 - 22:59
BOS
-
ORD
6h 21m
1 stop
JetBlue Logo
10:00 - 13:20
ORD
-
BOS
2h 20mdirect
₹ 12,843JetBlue
Tue, 3 Mar - Tue, 10 Mar
Delta Logo
07:15 - 09:25
BOS
-
ORD
3h 10mdirect
Delta Logo
06:15 - 09:40
ORD
-
BOS
2h 25mdirect
₹ 12,934Delta
Thu, 2 Apr - Sun, 5 Apr
JetBlue Logo
07:00 - 09:10
BOS
-
ORD
3h 10mdirect
JetBlue Logo
12:41 - 19:58
ORD
-
BOS
6h 17m
1 stop
₹ 13,115JetBlue
Mon, 9 Mar - Mon, 9 Mar
Delta Logo
17:15 - 19:23
BOS
-
ORD
3h 08mdirect
Delta Logo
19:35 - 23:02
ORD
-
BOS
2h 27mdirect
₹ 13,295Delta
Sat, 7 Mar - Mon, 9 Mar

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
11 Feb
BOS09:30Boston Logan Intl
3h 04m
ORD11:34Chicago O'Hare Intl
11 Feb
ORD18:05Chicago O'Hare Intl
2h 33m
BOS21:38Boston Logan Intl
₹ 12,210
United Airlines
3 Apr
BOS07:00Boston Logan Intl
3h 00m
ORD09:00Chicago O'Hare Intl
5 Apr
ORD07:30Chicago O'Hare Intl
2h 31m
BOS11:01Boston Logan Intl
₹ 12,391
United Airlines
5 Mar
BOS06:00Boston Logan Intl
3h 00m
ORD08:00Chicago O'Hare Intl
9 Mar
ORD21:15Chicago O'Hare Intl
2h 20m
BOS00:35Boston Logan Intl
₹ 12,572

Southwest flights from Boston to Chicago O'Hare Intl Airport

Our best Southwest deals on Boston to Chicago O'Hare Intl Airport flight tickets
Southwest
28 Feb
BOS05:55Boston Logan Intl
9h 10m
1 stop
ORD14:05Chicago O'Hare Intl
2 Mar
ORD13:45Chicago O'Hare Intl
8h 10m
1 stop
BOS22:55Boston Logan Intl
₹ 16,642
Southwest
23 Feb
BOS05:00Boston Logan Intl
8h 15m
1 stop
ORD12:15Chicago O'Hare Intl
27 Feb
ORD17:15Chicago O'Hare Intl
5h 55m
1 stop
BOS00:10Boston Logan Intl
₹ 16,823
Southwest
11 Feb
BOS09:35Boston Logan Intl
13h 15m
2 stops
ORD21:50Chicago O'Hare Intl
14 Feb
ORD15:45Chicago O'Hare Intl
5h 35m
1 stop
BOS22:20Boston Logan Intl
₹ 24,963

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 8 February 2026.
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

Fri 20/2

18:28-20:30

Nonstop3h 02m

Chicago O'Hare Intl

Tue 24/2

18:20-21:48

Nonstop2h 28m

₹ 12,210

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 27/2

07:00-09:10

Nonstop3h 10m

Chicago O'Hare Intl

Mon 2/3

10:00-13:20

Nonstop2h 20m

₹ 12,301

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 3/4

07:00-09:00

Nonstop3h 00m

Chicago O'Hare Intl

Sun 5/4

06:00-09:25

Nonstop2h 25m

₹ 12,391

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/3

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Mon 9/3

21:15-00:35

Nonstop2h 20m

₹ 12,572

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 26/2

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Sun 1/3

07:30-10:49

Nonstop2h 19m

₹ 12,662

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 29/3

06:00-07:59

Nonstop2h 59m

Chicago O'Hare Intl

Wed 1/4

09:15-12:46

Nonstop2h 31m

₹ 12,753

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/3

17:38-22:59

1 stop6h 21m

Chicago O'Hare Intl

Tue 10/3

10:00-13:20

Nonstop2h 20m

₹ 12,843

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/4

07:15-09:25

Nonstop3h 10m

Chicago O'Hare Intl

Sun 5/4

06:15-09:40

Nonstop2h 25m

₹ 12,934

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/3

07:00-09:10

Nonstop3h 10m

Chicago O'Hare Intl

Mon 9/3

12:41-19:58

1 stop6h 17m

₹ 13,115

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/3

17:15-19:23

Nonstop3h 08m

Chicago O'Hare Intl

Mon 9/3

19:35-23:02

Nonstop2h 27m

₹ 13,295

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 ₹ 18,722, 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 ₹ 18,722.

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 Saturday when prices can be found for as low as ₹ 14,196. 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 Friday because tickets tend to average around ₹ 29,210. 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 morning 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 ₹ 18,729. Flying to Chicago O'Hare Intl Airport in the morning 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 evening when prices are ₹ 25,029 on average. Flights to Chicago O'Hare Intl Airport from Boston in the evening 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 ₹ 22,415 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 ₹ 19,627 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 54% 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 February 2026, prices for Boston to Chicago O'Hare Intl Airport flights are approximately 16% more expensive 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

Fastest flight time

3h 07m

Direct flights

Every day
The fastest flight from Boston to Chicago O'Hare Intl Airport takes 3h 07m
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 3h 07m.

  • 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 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?

Travelling to a place near Chicago?

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

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.

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