BOS - ORD

£63 Find cheap flights from Boston to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Chicago departing on 21/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago, as well as popular online travel agencies
In the last 7 days, travellers have searched 46,646,933 times on KAYAK, and here's why:

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Cheap flight deals from Boston to Chicago (BOS-ORD)

 
These are the cheapest deals for flights from Boston to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent return flight deals from Boston to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Boston to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
06:00 - 08:05BOS-ORD
3h 05mdirect
16:40 - 20:02ORD-BOS
2h 22mdirect
£124JetBlue
Find Deal
Thu, 5 Dec - Tue, 10 Dec
07:20 - 09:29BOS-ORD
3h 09mdirect
06:30 - 10:00ORD-BOS
2h 30mdirect
£125Delta
Find Deal
Thu, 5 Dec - Mon, 9 Dec
06:00 - 08:06BOS-ORD
3h 06mdirect
10:14 - 15:43ORD-BOS
4h 29m1 stop
£127JetBlue
Find Deal
Tue, 17 Dec - Tue, 17 Dec
08:35 - 15:44BOS-ORD
8h 09m1 stop
07:00 - 10:15ORD-BOS
2h 15mdirect
£131JetBlue
Find Deal
Fri, 10 Jan - Mon, 13 Jan
06:00 - 10:53BOS-ORD
5h 53m1 stop
18:05 - 21:30ORD-BOS
2h 25mdirect
£132United Airlines
Find Deal
Thu, 5 Dec - Fri, 6 Dec
17:50 - 22:57BOS-ORD
6h 07m1 stop
10:50 - 16:05ORD-BOS
4h 15m1 stop
£139United Airlines
Find Deal
Sun, 2 Feb - Sat, 8 Feb
06:55 - 16:45BOS-ORD
10h 50m2 stops
13:30 - 19:50ORD-BOS
5h 20m1 stop
£199Southwest
Find Deal
Thu, 9 Jan - Sat, 11 Jan
07:20 - 22:20BOS-ORD
16h 00m2 stops
11:25 - 22:30ORD-BOS
10h 05m2 stops
£219Southwest
Find Deal
Mon, 20 Jan - Fri, 24 Jan
11:31 - 18:39BOS-ORD
8h 08m1 stop
18:50 - 10:35ORD-BOS
14h 45m1 stop
£234Sun Country Air
Find Deal
Fri, 25 Apr - Sun, 27 Apr
11:45 - 18:06BOS-ORD
7h 21m1 stop
21:13 - 10:42ORD-BOS
12h 29m1 stop
£249Sun Country Air
Find Deal
Fri, 11 Apr - Sun, 13 Apr

Flights from Boston to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Boston to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Boston to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Boston to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Boston to Chicago O'Hare Intl Airport is January, where tickets cost £154 on average. On the other hand, the most expensive months are May and November, where the average cost of tickets is £228 and £228 respectively.

Can I save money by flying with a stopover from Boston to Chicago O'Hare Intl Airport?

The average price for all direct flights, flights with one stopover, and flights with two stopovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of £200, prices are generally cheapest when you fly direct.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Boston to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Boston to Chicago O'Hare Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 151 days before departure.

Good to know - Cheap tickets from Boston to Chicago

Low season

January

High season

November

Cheapest flight

£63
Best time to beat the crowds (21% less expensive on average)
Most popular time to fly (18% more expensive on average)
Flight from Boston to Chicago

When to book flights from Boston to Chicago

Are your dates flexible? Find out the best times to travel from Boston to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Boston to Chicago flights

  • What can I do while waiting on my plane to leave the Chicago O'Hare Airport (ORD)?

    There is a public art exhibit at the Chicago O'Hare Airport (ORD). Throughout the airport, there are sculptures, paintings, murals, and photography that you can appreciate. There is also a yoga room where you can relax, a business center where you can catch up on e-mails, and many different airline lounges where members can enjoy a variety of benefits.

  • Where can I eat at the Boston Logan International Airport (BOS)?

    There are several places to eat while you're waiting on your plane to leave Boston. You can dine at Friendly's Restaurant, Sbarro, Potbelly Sandwich Shop, or WPizza by Wolfgang Puck. If you want something light to eat or a little java before you board, there is a Dunkin's Donut and several Starbucks around the airport.

  • How can I get to my hotel from the Chicago O'Hare International Airport (ORD)?

    Public transit is easily accessible from the airport. This includes a commuter train that goes from the airport into many areas of the city and its outlining communities. Known as the Metra Train, you'll catch it by taking the airport shuttle bus to the Multi-Modal Facility. The train station is a short walk from this building.

  • Is it easy to get around the Boston Logan International Airport (BOS)?

    The Boston Logan International Airport (BOS) has four terminals and 94 gates. There is a complimentary shuttle that takes passengers from one terminal to another. You can also take this shuttle to other parts of the airport including the rental car center and the airport train station.

  • What is the cheapest flight from Boston to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Boston to Chicago O'Hare Intl Airport was £79 for a one-way ticket and £157 for a return.

  • Which airports will I be using when flying from Boston to Chicago?

    On your way to Chicago, you’ll fly out from Boston Logan Intl. You’ll be landing at Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Boston to Chicago?

    American Airlines, Delta, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Boston to Chicago flight route.

  • Which aircraft models fly most regularly from Boston to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Boston to Chicago flight route.

  • Which airline alliances offer flights from Boston to Chicago?

    oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Boston and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Boston to Chicago?

    There are direct flights from Boston to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Boston to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Boston is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Boston with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Boston to Chicago O'Hare Intl Airport

  • Looking for a cheap flight from Chicago to Boston? 25% of our users found flights on this route for £70 or less one-way.
  • You'll easily find a nonstop flight going from Boston Logan International (BOS) to Chicago O-Hare International Airport (ORD). If you have a layover, you'll probably change planes in either Philadelphia, Detroit, or Washington, D.C. On average, these are short layovers of less than 2h.
  • If you drive yourself to Boston Logan International (BOS) for your trip, you'll have the option of parking in a garage or an uncovered parking lot. You can save money by parking in the economy garage which is just a few minutes from the airport. A complimentary shuttle will take you to the airport from the garage.
  • Withdraw money for your trip to Chicago at one of the ATM machines at the Boston Logan International Airport (BOS). There is an ATM machine in Terminal A, Terminal B, Terminal C, and Terminal E.
  • Amenities and services at the Boston Logan International Airport (BOS) include baggage trolleys, a shoe shine, hydration stations, a beauty salon where you can get a pedicure or manicure, a spa where you can relax with a massage, and several airport lounges with benefits like complimentary beverages, television, and comfortable seating.
  • Passengers who are delayed or have a late flight to Chicago will benefit from its on-site hotel. There is a Hilton Chicago O'Hare Hotel across from Terminals 1, 2, and 3. Along with sleeping rooms, the hotel has a variety of amenities such as a fitness center and sports bar.
See more tips

Prefer to fly direct from Boston to Chicago?

Find which airlines fly direct from Boston Logan Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Boston Logan Intl to Chicago O'Hare Intl

Monday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +18 more

ANA, Air New Zealand, +19 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +17 more

ANA, Air New Zealand, +18 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Friday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +19 more

ANA, Air New Zealand, +20 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Boston Logan Intl

Monday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Friday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

See more direct flights
See more direct flights

Book cheap flights from Boston to Chicago

Cheapest flights to Chicago from Boston found in 2024 and 2025

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Boston to Chicago found on KAYAK in the last 72 hours.
21/1Tue
directDelta
3h 10mBOS-ORD
£63
9/1Thu
1 stopJetBlue
5h 16mBOS-ORD
£70
10/1Fri
directJetBlue
3h 04mBOS-ORD
£70
31/12Tue
directUnited Airlines
3h 03mBOS-ORD
£75
25/12Wed
directUnited Airlines
3h 03mBOS-ORD
£90
18/2Tue
1 stopSouthwest
7h 45mBOS-ORD
£93
5/1Sun
1 stopSouthwest
4h 45mBOS-ORD
£102
15/1Wed
1 stopAlaska Airlines
31h 04mBOS-ORD
£156
27/12Fri
1 stopSun Country Air
12h 53mBOS-ORD
£208
1/12Sun
1 stopSun Country Air
22h 51mBOS-ORD
£331

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Last minute flights from Boston to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Boston to Chicago that are departing in the next 10 days.
26/11Tue
directDelta
3h 09mBOS-ORD
4/12Wed
directDelta
2h 20mORD-BOS
£200
26/11Tue
directDelta
3h 09mBOS-ORD
29/11Fri
directDelta
2h 24mORD-BOS
£212
24/11Sun
multi-stopDelta
6h 31mBOS-ORD
29/11Fri
directDelta
2h 24mORD-BOS
£220
24/11Sun
directDelta
2h 58mBOS-ORD
4/12Wed
directDelta
2h 20mORD-BOS
£235
24/11Sun
directJetBlue
3h 07mBOS-ORD
3/12Tue
directJetBlue
2h 20mORD-BOS
£247
23/11Sat
directJetBlue
3h 09mBOS-ORD
26/11Tue
directJetBlue
2h 13mORD-BOS
£275
24/11Sun
multi-stopSouthwest
9h 00mBOS-ORD
27/11Wed
multi-stopSouthwest
16h 25mORD-BOS
£282
26/11Tue
directUnited Airlines
2h 56mBOS-ORD
1/12Sun
directUnited Airlines
2h 19mORD-BOS
£291
25/11Mon
multi-stopSouthwest
9h 20mBOS-ORD
2/12Mon
multi-stopSouthwest
16h 25mORD-BOS
£294
26/11Tue
multi-stopUnited Airlines
7h 04mBOS-ORD
1/12Sun
directUnited Airlines
2h 19mORD-BOS
£299

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Everything you need to know for your flight from Boston to Chicago

Information on your arrival and departure airports

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