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Find cheap flights from Boston to Chicago from £52

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 14/5. 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.
1 adult
0 bags
Fri 24/5
Fri 31/5

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 44,632,927 times on KAYAK, and here's why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
06:10 - 08:04BOS-ORD
2h 54mdirect
19:15 - 22:41ORD-BOS
2h 26mdirect
£102JetBlue
Find Deal
Wed, 29 May - Wed, 29 May
08:05 - 10:03BOS-ORD
2h 58mdirect
06:27 - 09:54ORD-BOS
2h 27mdirect
£115Delta
Find Deal
Sun, 26 May - Wed, 29 May
14:10 - 16:04BOS-ORD
2h 54mdirect
06:27 - 09:54ORD-BOS
2h 27mdirect
£119Delta
Find Deal
Tue, 28 May - Wed, 29 May
06:10 - 08:04BOS-ORD
2h 54mdirect
19:15 - 22:41ORD-BOS
2h 26mdirect
£123JetBlue
Find Deal
Tue, 4 Jun - Fri, 7 Jun
13:38 - 17:25BOS-ORD
4h 47m1 stop
16:53 - 22:08ORD-BOS
4h 15m1 stop
£175American Airlines
Find Deal
Thu, 9 May - Mon, 13 May
05:45 - 16:25BOS-ORD
11h 40m1 stop
17:25 - 22:55ORD-BOS
4h 30m1 stop
£186Southwest
Find Deal
Tue, 21 May - Wed, 22 May
05:45 - 16:25BOS-ORD
11h 40m1 stop
17:25 - 22:55ORD-BOS
4h 30m1 stop
£193Southwest
Find Deal
Tue, 21 May - Wed, 22 May
11:27 - 18:17BOS-ORD
7h 50m1 stop
05:33 - 11:57ORD-BOS
5h 24m1 stop
Fri, 24 May - Tue, 28 May
11:39 - 19:08BOS-ORD
8h 29m1 stop
19:15 - 10:40ORD-BOS
14h 25m1 stop
£214Sun Country Air
Find Deal
Fri, 27 Sep - Sun, 29 Sep
05:25 - 07:21BOS-ORD
2h 56mdirect
16:53 - 23:30ORD-BOS
5h 37m1 stop
£219American Airlines
Find Deal
Fri, 24 May - Tue, 28 May

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 February, where tickets cost £128 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is £294 and £263 respectively.

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 87 days before departure.

Which airlines provide the cheapest flights from Boston to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Boston to Chicago found by KAYAK users in the last 72 hours was for £102 on JetBlue, followed by Delta (£115). One-way flight deals have also been found from as low as £52 on JetBlue and from £56 on Delta.

How many flights are there between Boston and Chicago O'Hare Intl Airport per day?

Each day, there are between 27 and 38 nonstop flights that take off from Boston and land in Chicago O'Hare Intl Airport, with an average flight time of 2h 55m. The most common departure time is 15:00 and most flights take off in the afternoon. Each week, there are 226 flights. The most frequent day of departure is Friday, when 17% of all weekly flights depart. The fewest flights depart on a Wednesday.

Which cabin class options are there for flights between Boston and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 2 cabin class options for the route. These are Business and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Boston to Chicago take?

Direct flights from Boston generally make it to Chicago in 2h 45m. The flying distance between the two cities is 864 miles.

What’s the earliest departure time from Boston to Chicago?

Early birds can take the earliest flight from Boston at 05:25 and will be landing in Chicago O'Hare Intl Airport at 07:21.

What’s the latest departure time from Boston to Chicago?

If you prefer to fly at night, the latest flight from Boston to Chicago O'Hare Intl Airport jets off at 20:55 and lands at 22:52.

Good to know - Cheap tickets from Boston to Chicago

Low season

January

High season

November

Cheapest flight

£52
Best time to beat the crowds (37% less expensive on average)
Most popular time to fly (13% 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 £64 for a one-way ticket and £127 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, SkyTeam, and Star Alliance 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

Top tips for finding a cheap flight from Boston to Chicago

  • Looking for a cheap flight from Chicago to Boston? 25% of our users found flights on this route for £129 or less one-way and £176 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 Logan Intl to O'Hare Intl, 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, +22 more

ANA, Air New Zealand, +23 more

Tuesday

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

ANA, Air New Zealand, +21 more

Wednesday

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

ANA, Air New Zealand, +23 more

Thursday

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

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

ANA, Air New Zealand, +24 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Boston Logan Intl

Monday

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

ANA, Air New Zealand, +22 more

Tuesday

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

ANA, Air New Zealand, +21 more

Wednesday

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

ANA, Air New Zealand, +23 more

Thursday

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

ANA, Air New Zealand, +22 more

Friday

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

ANA, Air New Zealand, +23 more

Saturday

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

ANA, Air New Zealand, +21 more

Sunday

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

ANA, Air New Zealand, +24 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

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.
14/5Tue
directJetBlue
2h 54mBOS-ORD
£52
26/5Sun
directDelta
2h 58mBOS-ORD
£56
28/5Tue
directDelta
2h 54mBOS-ORD
£60
3/7Wed
directSpirit Airlines
2h 33mBOS-ORD
£66
27/6Thu
1 stopAmerican Airlines
6h 18mBOS-ORD
£100
30/5Thu
1 stopSouthwest
9h 50mBOS-ORD
£103
30/4Tue
1 stopSouthwest
11h 40mBOS-ORD
£107
3/7Wed
1 stopAmerican Airlines
4h 42mBOS-ORD
£123
7/7Sun
directUnited Airlines
2h 46mBOS-ORD
£125
30/4Tue
2 stopsUnited Airlines
13h 55mBOS-ORD
£169

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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.
28/4Sun
directJetBlue
2h 58mBOS-ORD
29/4Mon
directJetBlue
2h 29mORD-BOS
£201
27/4Sat
directJetBlue
2h 54mBOS-ORD
8/5Wed
directJetBlue
2h 29mORD-BOS
£217
27/4Sat
multi-stopDelta
6h 46mBOS-ORD
1/5Wed
directDelta
2h 32mORD-BOS
£236
26/4Fri
directDelta
2h 56mBOS-ORD
29/4Mon
directDelta
2h 32mORD-BOS
£245
26/4Fri
directAmerican Airlines
2h 58mBOS-ORD
28/4Sun
directAmerican Airlines
2h 29mORD-BOS
£289
26/4Fri
directAmerican Airlines
3h 06mBOS-ORD
28/4Sun
directAmerican Airlines
2h 29mORD-BOS
£294
28/4Sun
multi-stopSouthwest
5h 20mBOS-ORD
29/4Mon
multi-stopSouthwest
4h 35mORD-BOS
£323
26/4Fri
directUnited Airlines
2h 54mBOS-ORD
28/4Sun
directUnited Airlines
2h 23mORD-BOS
£358
26/4Fri
directUnited Airlines
2h 48mBOS-ORD
28/4Sun
multi-stopUnited Airlines
6h 30mORD-BOS
£363
28/4Sun
multi-stopSouthwest
13h 10mBOS-ORD
29/4Mon
multi-stopSouthwest
10h 40mORD-BOS
£487

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Boston - Chicago Flights

Departure:

Boston (BOS)United States

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Boston

Cabin classes:

£3,654
£87

Browse origins:

  • Flights » 
  • Boston

Browse destinations:

  • Flights » 
  • Worldwide » 
  • Chicago » 
  • Chicago O'Hare Airport