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BOS - ORD

£46 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 5/2. 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 46,479,581 times on KAYAK, and here's why:

Save 31% or moreCompare multiple travel sites with one search.

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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.

Recent one-way flight deals from Boston to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Boston to Chicago found on KAYAK recently.

Recent last-minute flight deals from Boston to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Boston to Chicago.

Recent direct flight deals from Boston to Chicago

The latest deals for direct flights from Boston to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Boston to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:05 - 13:03BOS-ORD
2h 58mdirect
14:05 - 17:34ORD-BOS
2h 29mdirect
£90Delta
Find Deal
mié., 4 dic. - lun., 9 dic.
06:00 - 08:06BOS-ORD
3h 06mdirect
16:40 - 20:02ORD-BOS
2h 22mdirect
£93JetBlue
Find Deal
vie., 13 dic. - mar., 17 dic.
06:00 - 08:06BOS-ORD
3h 06mdirect
10:14 - 15:43ORD-BOS
4h 29m1 stop
£94JetBlue
Find Deal
lun., 9 dic. - lun., 9 dic.
06:00 - 08:06BOS-ORD
3h 06mdirect
08:51 - 12:13ORD-BOS
2h 22mdirect
£95JetBlue
Find Deal
vie., 6 dic. - dom., 8 dic.
06:00 - 08:05BOS-ORD
3h 05mdirect
10:14 - 15:43ORD-BOS
4h 29m1 stop
£97JetBlue
Find Deal
mié., 4 dic. - lun., 9 dic.
07:20 - 09:29BOS-ORD
3h 09mdirect
06:40 - 10:00ORD-BOS
2h 20mdirect
£107Delta
Find Deal
jue., 14 nov. - lun., 18 nov.
06:02 - 08:05BOS-ORD
3h 03mdirect
15:42 - 22:00ORD-BOS
5h 18m1 stop
£130United Airlines
Find Deal
mar., 31 dic. - sáb., 4 ene.
05:45 - 09:34BOS-ORD
4h 49m1 stop
12:53 - 18:33ORD-BOS
4h 40m1 stop
£136United Airlines
Find Deal
dom., 15 dic. - mar., 17 dic.
05:25 - 11:30BOS-ORD
7h 05m1 stop
17:45 - 08:20ORD-BOS
13h 35m2 stops
£158Southwest
Find Deal
sáb., 16 nov. - lun., 18 nov.
07:05 - 21:30BOS-ORD
15h 25m2 stops
17:45 - 08:20ORD-BOS
13h 35m2 stops
£213Southwest
Find Deal
vie., 15 nov. - lun., 18 nov.
11:00 - 13:08BOS-ORD
3h 08mdirect
£46Delta
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mié., 5 feb.
06:00 - 08:06BOS-ORD
3h 06mdirect
£48JetBlue
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dom., 8 dic.
05:45 - 09:34BOS-ORD
4h 49m1 stop
£68United Airlines
Find Deal
dom., 15 dic.
06:00 - 08:03BOS-ORD
3h 03mdirect
£73United Airlines
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sáb., 1 feb.
11:37 - 11:35BOS-ORD
24h 58m1 stop
£99Sun Country Air
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sáb., 14 dic.
06:15 - 16:45BOS-ORD
11h 30m1 stop
£106Southwest
Find Deal
vie., 15 nov.
10:45 - 22:35BOS-ORD
12h 50m2 stops
£108Southwest
Find Deal
vie., 15 nov.
06:45 - 18:38BOS-ORD
12h 53m1 stop
£122Sun Country Air
Find Deal
vie., 27 dic.
17:55 - 23:59BOS-ORD
31h 04m1 stop
£129Alaska Airlines
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sáb., 1 feb.
16:23 - 17:00BOS-ORD
25h 37m2 stops
£176Alaska Airlines
Find Deal
vie., 21 feb.
18:55 - 20:54BOS-ORD
2h 59mdirect
14:05 - 17:30ORD-BOS
2h 25mdirect
£179Delta
Find Deal
mar., 5 nov. - mar., 19 nov.
17:25 - 23:00BOS-ORD
6h 35m1 stop
21:35 - 00:54ORD-BOS
2h 19mdirect
£183United Airlines
Find Deal
mié., 6 nov. - vie., 8 nov.
11:00 - 16:35BOS-ORD
6h 35m1 stop
06:40 - 10:00ORD-BOS
2h 20mdirect
£187Delta
Find Deal
mar., 5 nov. - mar., 19 nov.
15:55 - 17:51BOS-ORD
2h 56mdirect
06:40 - 10:00ORD-BOS
2h 20mdirect
£195Delta
Find Deal
lun., 4 nov. - dom., 17 nov.
19:40 - 21:32BOS-ORD
2h 52mdirect
17:40 - 21:01ORD-BOS
2h 21mdirect
£199Delta
Find Deal
sáb., 2 nov. - sáb., 16 nov.
05:01 - 09:03BOS-ORD
5h 02m1 stop
09:48 - 18:36ORD-BOS
7h 48m1 stop
£217JetBlue
Find Deal
dom., 3 nov. - mar., 19 nov.
06:00 - 08:06BOS-ORD
3h 06mdirect
09:56 - 13:14ORD-BOS
2h 18mdirect
£226JetBlue
Find Deal
mar., 5 nov. - sáb., 16 nov.
05:40 - 13:00BOS-ORD
8h 20m1 stop
16:00 - 01:05ORD-BOS
8h 05m1 stop
£239Southwest
Find Deal
mié., 6 nov. - vie., 8 nov.
05:45 - 14:15BOS-ORD
9h 30m2 stops
11:25 - 22:05ORD-BOS
9h 40m2 stops
£275Southwest
Find Deal
sáb., 2 nov. - sáb., 16 nov.
16:36 - 14:02BOS-ORD
22h 26m2 stops
07:00 - 18:59ORD-BOS
10h 59m1 stop
£2,414Alaska Airlines
Find Deal
sáb., 2 nov. - mar., 5 nov.
06:00 - 08:05BOS-ORD
3h 05mdirect
08:51 - 12:13ORD-BOS
2h 22mdirect
£90JetBlue
Find Deal
mié., 4 dic. - mar., 10 dic.
06:00 - 08:06BOS-ORD
3h 06mdirect
16:40 - 20:02ORD-BOS
2h 22mdirect
£93JetBlue
Find Deal
vie., 13 dic. - mar., 17 dic.
06:00 - 08:06BOS-ORD
3h 06mdirect
08:51 - 12:13ORD-BOS
2h 22mdirect
£95JetBlue
Find Deal
vie., 6 dic. - dom., 8 dic.
06:00 - 08:06BOS-ORD
3h 06mdirect
08:51 - 12:13ORD-BOS
2h 22mdirect
£106JetBlue
Find Deal
vie., 6 dic. - mié., 11 dic.
07:20 - 09:29BOS-ORD
3h 09mdirect
06:40 - 10:00ORD-BOS
2h 20mdirect
£107Delta
Find Deal
jue., 14 nov. - lun., 18 nov.
15:45 - 17:46BOS-ORD
3h 01mdirect
07:15 - 10:40ORD-BOS
2h 25mdirect
£114Delta
Find Deal
jue., 21 nov. - sáb., 23 nov.
07:25 - 09:28BOS-ORD
3h 03mdirect
06:30 - 10:00ORD-BOS
2h 30mdirect
£121Delta
Find Deal
vie., 6 dic. - dom., 8 dic.
18:28 - 20:24BOS-ORD
2h 56mdirect
13:55 - 17:16ORD-BOS
2h 21mdirect
£141United Airlines
Find Deal
mar., 12 nov. - sáb., 16 nov.
06:00 - 07:56BOS-ORD
2h 56mdirect
13:55 - 17:16ORD-BOS
2h 21mdirect
£146United Airlines
Find Deal
vie., 22 nov. - vie., 22 nov.
06:00 - 07:56BOS-ORD
2h 56mdirect
21:35 - 00:54ORD-BOS
2h 19mdirect
£149United Airlines
Find Deal
lun., 25 nov. - mié., 27 nov.

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 September, where tickets cost £148 on average. On the other hand, the most expensive months are November and May, where the average cost of tickets is £228 and £223 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 £178, 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

£46
Best time to beat the crowds (21% less expensive on average)
Most popular time to fly (19% 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 £59 for a one-way ticket and £117 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 £68 or less one-way and £127 or less round-trip.
  • 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, +21 more

ANA, Air New Zealand, +22 more

Wednesday

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

ANA, Air New Zealand, +20 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +23 more

ANA, Air New Zealand, +24 more

Friday

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

ANA, Air New Zealand, +23 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

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, +20 more

ANA, Air New Zealand, +21 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.
5/2mié.
directDelta
3h 08mBOS-ORD
£46
8/12dom.
directJetBlue
3h 06mBOS-ORD
£48
15/12dom.
1 stopUnited Airlines
4h 49mBOS-ORD
£68
1/2sáb.
directUnited Airlines
3h 03mBOS-ORD
£73
14/12sáb.
1 stopSun Country Air
24h 58mBOS-ORD
£99
15/11vie.
1 stopSouthwest
11h 30mBOS-ORD
£106
15/11vie.
2 stopsSouthwest
12h 50mBOS-ORD
£108
27/12vie.
1 stopSun Country Air
12h 53mBOS-ORD
£122
1/2sáb.
1 stopAlaska Airlines
31h 04mBOS-ORD
£129
21/2vie.
2 stopsAlaska Airlines
25h 37mBOS-ORD
£176

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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.
5/11mar.
directDelta
2h 59mBOS-ORD
19/11mar.
directDelta
2h 25mORD-BOS
£179
6/11mié.
multi-stopUnited Airlines
6h 35mBOS-ORD
8/11vie.
directUnited Airlines
2h 19mORD-BOS
£183
5/11mar.
multi-stopDelta
6h 35mBOS-ORD
19/11mar.
directDelta
2h 20mORD-BOS
£187
4/11lun.
directDelta
2h 56mBOS-ORD
17/11dom.
directDelta
2h 20mORD-BOS
£195
2/11sáb.
directDelta
2h 52mBOS-ORD
16/11sáb.
directDelta
2h 21mORD-BOS
£199
3/11dom.
multi-stopJetBlue
5h 02mBOS-ORD
19/11mar.
multi-stopJetBlue
7h 48mORD-BOS
£217
5/11mar.
directJetBlue
3h 06mBOS-ORD
16/11sáb.
directJetBlue
2h 18mORD-BOS
£226
6/11mié.
multi-stopSouthwest
8h 20mBOS-ORD
8/11vie.
multi-stopSouthwest
8h 05mORD-BOS
£239
2/11sáb.
multi-stopSouthwest
9h 30mBOS-ORD
16/11sáb.
multi-stopSouthwest
9h 40mORD-BOS
£275
2/11sáb.
multi-stopAlaska Airlines
22h 26mBOS-ORD
5/11mar.
multi-stopAlaska Airlines
10h 59mORD-BOS
£2,414

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

Information on your arrival and departure airports