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Find cheap flights from Chicago to Boston from £55

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Boston departing on 6/8. 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 7/6
Fri 14/6

Search hundreds of travel sites at once for deals on flights to Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston, 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 Chicago to Boston, as well as popular online travel agencies
In the last 7 days, travellers have searched 43,968,530 times on KAYAK, and here's why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Boston 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
20:02 - 23:31ORD-BOS
2h 29mdirect
06:30 - 08:24BOS-ORD
2h 54mdirect
£66Spirit Airlines
Find Deal
Wed, 19 Jun - Wed, 26 Jun
20:02 - 23:31ORD-BOS
2h 29mdirect
12:07 - 19:05BOS-ORD
7h 58m1 stop
£73Spirit Airlines
Find Deal
Wed, 19 Jun - Wed, 26 Jun
20:02 - 23:31ORD-BOS
2h 29mdirect
06:30 - 08:24BOS-ORD
2h 54mdirect
£75Spirit Airlines
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Wed, 19 Jun - Tue, 25 Jun
19:15 - 22:41ORD-BOS
2h 26mdirect
06:10 - 08:04BOS-ORD
2h 54mdirect
£109JetBlue
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Wed, 29 May - Wed, 5 Jun
19:15 - 22:41ORD-BOS
2h 26mdirect
16:25 - 18:20BOS-ORD
2h 55mdirect
£117JetBlue
Find Deal
Wed, 29 May - Sat, 1 Jun
13:50 - 17:18ORD-BOS
2h 28mdirect
07:00 - 08:57BOS-ORD
2h 57mdirect
£126Delta
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Wed, 4 Sep - Wed, 11 Sep
20:05 - 10:36ORD-BOS
13h 31m1 stop
13:53 - 23:45BOS-ORD
10h 52m1 stop
Wed, 19 Jun - Tue, 25 Jun
17:15 - 20:44ORD-BOS
2h 29mdirect
17:05 - 19:03BOS-ORD
2h 58mdirect
£133Delta
Find Deal
Sat, 1 Jun - Sat, 8 Jun
20:30 - 10:33ORD-BOS
13h 03m1 stop
09:00 - 17:18BOS-ORD
9h 18m1 stop
£183Sun Country Air
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Fri, 31 May - Mon, 3 Jun
18:15 - 10:23ORD-BOS
15h 08m1 stop
11:26 - 17:35BOS-ORD
7h 09m1 stop
£211Sun Country Air
Find Deal
Mon, 3 Jun - Thu, 6 Jun

Flights from Chicago to Boston - Travel Insights & Trends

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago O'Hare Intl Airport to Boston, 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 Chicago O'Hare Intl Airport to Boston is January, where tickets cost £160 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is £262 and £251 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago O'Hare Intl Airport to Boston, 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 Chicago O'Hare Intl Airport to Boston, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 84 days before departure.

Which airlines provide the cheapest flights from Chicago to Boston?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Chicago to Boston found on KAYAK was with Delta for £55. Spirit Airlines proposed a return connection from £66 and JetBlue from £109.

Which airlines fly most frequently between Chicago and Boston?

American Airlines connects Chicago to Boston with up to 11 flights per day. United Airlines also offers 11 flights per day, while Delta follows with 6 flights per day.

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

Each day, there are between 31 and 35 nonstop flights that take off from Chicago O'Hare Intl Airport and land in Boston, with an average flight time of 2h 26m. The most common departure time is 13:00 and most flights take off in the morning. Each week, there are 230 flights. The most frequent day of departure is Friday, when 15% of all weekly flights depart. The fewest flights depart on a Monday.

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

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 3 cabin class options for the route. These are First, 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 Chicago to Boston take?

Direct flights from Chicago generally make it to Boston in 2h 12m. The flying distance between the two cities is 864 miles.

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

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 06:04 and will be landing in Boston at 09:24.

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

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Boston jets off at 21:45 and lands at 01:06.

Good to know - Cheap tickets from Chicago to Boston

Low season

January

High season

September

Cheapest flight

£55
Best time to beat the crowds (30% less expensive on average)
Most popular time to fly and prices are also 14% lower on average.
Flight from Chicago to Boston

When to book flights from Chicago to Boston

Are your dates flexible? Find out the best times to travel from Chicago to Boston 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 Chicago to Boston flights

  • If you arrive at ORD airport early, what activities can you do to pass the time?

    There is a yoga room with mats where passengers can practice yoga, relax, and meditate as they wait for their flights. It is located on the mezzanine level of terminal 3. For those interested in the arts, there is a public art program with sculptures and paintings where you can browse art pieces before flying.

  • If you have an early morning flight, where can you spend the night in ORD?

    You can spend your night at the Hilton Chicago O'Hare airport hotel found within the airport grounds. It is located near terminals 1, 2, and 3, and you can walk from the airport to the hotel. The hotel has a fitness center, showers, restaurant, and elegant rooms.

  • Which family services are offered at ORD airport?

    ORD has a family lounge near gate F1 in terminal 2. The lounge has space where kids can play and stroller parking for passengers traveling with infants. Nursing rooms are also available in every terminal. They provide a clean and safe space for nursing parents to pump and breastfeed their babies. The rooms have changing tables, comfortable seats, and soft lighting, making them comfortable for lactating parents. Most restrooms in the terminals have changing stations for young children.

  • Are there child-friendly restaurants in ORD?

    Many restaurants offer high chairs and a children's menu. Some restaurants in ORD provide a fantastic view of the airplanes landing and taking off. These restaurants include Berghoff Café and the Food Court seating area found at terminal 1 near Gate C. Other restaurants like Tuscany at gate B18 in Terminal 1 have a view of the airplanes on the ground.

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Boston was £69 for a one-way ticket and £83 for a return.

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

    All the following airlines offer inflight Wi-Fi service on the Chicago to Boston flight route: American Airlines, Delta, JetBlue, British Airways, Finnair, and Iberia.

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

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

  • Which airline alliances offer flights from Chicago to Boston?

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

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

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

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

    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 Chicago to Boston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago 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 Chicago to Boston?

    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 Boston with an airline and back to Chicago with another airline.

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

    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 Boston from Chicago 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 Chicago to Boston

  • Looking for a cheap flight from Boston to Chicago? 25% of our users found flights on this route for £173 or less one-way and £153 or less round-trip.
  • If you are in Chicago O'Hare International Airport (ORD) and you lose items at the security lines or checkpoints, you can ask the security guards to help you locate them. If things get lost on the flight, contact your airline for assistance.
  • Passengers transiting throughinORD can stay connected while waiting for their flight. Every terminal has free Wi-Fi access. Changing stations are available in the seating areas to ensure your device's battery stays full.
  • If you want a place to pray and relax while waiting for your flight in ORD, there is a multi-faith chapel found at terminal 2 on the mezzanine level. Boston Logan International Airport (BOS) also has a place where you can pray. In the terminal C pre-security area, there is a chapel known as Our Lady of the Airways Chapel.
  • If you are traveling with your pet, ORD has six animal relief areas- four outdoor areas and two after airport security. ORD pet policy states that when traveling with a pet, they should be carried inside a crate or carrier at the airport.
  • If you want to travel from BOS to downtown Boston, you can take the MBTA into Boston. It is the most efficient and cost-effective way to reach the city from BOS. The air shuttle offers free shuttle services from the airport station to the rental car center, water taxi, and airline terminals.
See more tips

Prefer to fly direct from Chicago to Boston?

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

Direct departures

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, +19 more

ANA, Air New Zealand, +20 more

Wednesday

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

ANA, Air New Zealand, +22 more

Thursday

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

ANA, Air New Zealand, +21 more

Friday

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

ANA, Air New Zealand, +22 more

Saturday

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

ANA, Air New Zealand, +20 more

Sunday

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

ANA, Air New Zealand, +23 more

See more direct flights

Direct returns

Boston Logan Intl to Chicago O'Hare Intl

Monday

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

ANA, Air New Zealand, +22 more

Tuesday

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

ANA, Air New Zealand, +20 more

Wednesday

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

ANA, Air New Zealand, +22 more

Thursday

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

ANA, Air New Zealand, +22 more

Friday

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

ANA, Air New Zealand, +22 more

Saturday

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

ANA, Air New Zealand, +21 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 Chicago to Boston

Cheapest flights to Boston from Chicago found in 2024

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Boston found on KAYAK in the last 72 hours.
6/8Tue
directDelta
2h 12mORD-BOS
£55
17/7Wed
directDelta
2h 28mORD-BOS
£71
18/5Sat
directJetBlue
2h 29mORD-BOS
£79
5/7Fri
1 stopJetBlue
5h 10mORD-BOS
£86
10/6Mon
directUnited Airlines
2h 35mORD-BOS
£147
13/5Mon
1 stopSouthwest
10h 40mORD-BOS
£163
18/8Sun
directUnited Airlines
2h 22mORD-BOS
£177
8/6Sat
2 stopsAlaska Airlines
14h 59mORD-BOS
£209
10/6Mon
2 stopsSouthwest
24h 55mORD-BOS
£211
31/10Thu
2 stopsAlaska Airlines
15h 59mORD-BOS
£229

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Last minute flights from Chicago to Boston

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 Chicago to Boston that are departing in the next 10 days.
13/5Mon
directJetBlue
2h 26mORD-BOS
18/5Sat
directJetBlue
2h 54mBOS-ORD
£178
13/5Mon
multi-stopFrontier
22h 43mORD-BOS
16/5Thu
multi-stopFrontier
15h 42mBOS-ORD
£183
13/5Mon
multi-stopFrontier
22h 43mORD-BOS
16/5Thu
multi-stopFrontier
15h 42mBOS-ORD
£199
10/5Fri
directDelta
2h 36mORD-BOS
14/5Tue
directDelta
2h 55mBOS-ORD
£226
9/5Thu
directDelta
2h 28mORD-BOS
14/5Tue
directDelta
3h 02mBOS-ORD
£229
13/5Mon
multi-stopAmerican Airlines
4h 44mORD-BOS
16/5Thu
directAmerican Airlines
2h 56mBOS-ORD
£232
13/5Mon
multi-stopSpirit Airlines
25h 01mORD-BOS
16/5Thu
multi-stopSpirit Airlines
13h 41mBOS-ORD
£241
13/5Mon
multi-stopSpirit Airlines
25h 01mORD-BOS
16/5Thu
multi-stopSpirit Airlines
22h 15mBOS-ORD
£299
13/5Mon
multi-stop
26h 26mORD-BOS
16/5Thu
multi-stop
13h 41mBOS-ORD
£335
13/5Mon
multi-stop
26h 26mORD-BOS
16/5Thu
multi-stop
30h 10mBOS-ORD
£495

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Chicago - Boston Flights

Departure:

Chicago (undefined)United States

Destination:

Boston (BOS)United States

Return flight deals:

Boston - Chicago

Cabin classes:

£110

Browse origins:

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

Browse destinations:

  • Flights » 
  • Worldwide » 
  • Boston