Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Chicago to Boston from £51

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
9 Jul — 16 Jul1
1 adult

Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in August or September, booked 73 days in advance, depart on a Saturday or Monday and return on a Thursday

Cheap flight deals from Chicago to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Boston (BOS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 4 July 2025.

Round-trip from

£100

One-way from

£51

Popular in

April

Cheapest in

August

Average price

£165

Good one-way deal

£76 or less
JetBlue
  • JetBlue
  • 8/10-14/10
  • Nonstop
  • 5h 30m total
  • Chicago to Boston
United Airlines
  • United Airlines
  • 7/8
  • Nonstop
  • 2h 26m total
  • Chicago to Boston
Highest demand for flights based on searches. 8% potential increase in price (£11 potential increase over avg. return price).
Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
Average for round-trip flights in July 2025
Price to beat on a one-way flight from Chicago (CHI) to Boston Logan Intl.

Find flight deals from Chicago to Boston

Cheapest flights from Chicago to Boston
Explore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 4 July 2025.

Wed 8/1018:50ORD - BOS
Nonstop2h 33mJetBlue
Thu 16/1016:05BOS - ORD
Nonstop2h 50mJetBlue
Deal found 3/7£100
Tue 5/807:30ORD - BOS
Nonstop2h 27mUnited Airlines
Tue 12/819:04BOS - ORD
1 stop5h 37mUnited Airlines
Deal found 1/7£105
Sat 23/807:00ORD - BOS
Nonstop2h 29mDelta
Sun 31/811:34BOS - ORD
Nonstop2h 51mDelta
Deal found 3/7£114
Sat 9/814:55ORD - BOS
1 stop5h 00mSouthwest
Wed 13/805:40BOS - ORD
1 stop7h 10mSouthwest
Deal found 4/7£115
Fri 25/718:02ORD - BOS
2 stops24h 32mSpirit Airlines
Tue 29/720:39BOS - ORD
1 stop13h 16mSpirit Airlines
Deal found 2/7£126

Cheapflights Fare Finder

Customise your flight search to find flights from Chicago to Boston 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, Cheapflights users made 858,174 searches. Data last updated 4 July 2025.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.

Fly from

Chicago

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/10

18:50-22:23

Nonstop2h 33m

Boston Logan Intl

Thu 16/10

16:05-17:55

Nonstop2h 50m

£100

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 25/7

20:30-00:14

Nonstop2h 44m

Boston Logan Intl

Tue 29/7

05:00-06:58

Nonstop2h 58m

£101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/8

07:30-10:57

Nonstop2h 27m

Boston Logan Intl

Tue 12/8

19:04-23:41

1 stop5h 37m

£105

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 23/8

07:00-10:29

Nonstop2h 29m

Boston Logan Intl

Sun 31/8

11:34-13:25

Nonstop2h 51m

£114

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/8

14:55-20:55

1 stop5h 00m

Boston Logan Intl

Tue 12/8

05:40-11:50

1 stop7h 10m

£115

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 25/7

18:02-19:34

2 stops24h 32m

Boston Logan Intl

Tue 29/7

20:39-08:55

1 stop13h 16m

£126

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 7/8

06:00-09:26

Nonstop2h 26m

£51

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 19/8

20:12-11:18

1 stop14h 06m

£51

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 19/7

13:30-21:05

1 stop6h 35m

£58

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 25/8

06:15-12:15

1 stop5h 00m

£86

Flights are sorted by cheapest return flights first.

Deals found on 3/7

Showing 1-10 of 12 results
1
2

Best time to book a flight from Chicago to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Chicago with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Boston?

Use this chart to determine the optimal time to book a return flight from Chicago to Boston. Price data was last updated on 27 June 2025.

Booking 73 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Boston?

Currently, October is the cheapest month in which you can book a flight from Chicago to Boston (average of £10). Flying from Chicago to Boston in July is currently the most expensive (average of £724). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to BOS?

Find hourly flight availability from Chicago to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 4 July 2025.

When flying from Chicago to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight at midday, which can drop the price by up to 68% versus a flight in the afternoon.

Weekly flight availability from Chicago to Boston

Explore weekly flight availability from Chicago to Boston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 4 July 2025.

The most flights from CHI to BOS are scheduled on a Thursday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Boston. Reviews last updated 4 July 2025.
Read reviews from past customers who have flown with Southwest, Delta, andUnited Airlines from Chicago to Boston. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
8.0
Very Good

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly into for flights to Boston from Chicago?

    Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago. On average, Logan Intl has 37 inbound flights from Chicago per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • What are the cheapest airlines flying from Chicago to Boston round-trip?

    Flying on JetBlue is currently your cheapest option to Boston, with prices starting at £100. Additional return tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at £101 and £105, respectively. You may be able to fly from Chicago to Boston for 39% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Boston one-way?

    One-way options have recently been found by users for as low as £51 on United Airlines. Other airlines that offer cheap prices include Spirit Airlines from £51 and Southwest from £58 one-way.

  • What are the most reliable airlines from Chicago to Boston?

    No one likes to see their flight delayed. When booking a flight from Chicago to Boston consider choosing Etihad Airways (92%), Royal Jordanian (83%) or EL AL (80%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Boston?

    The cheapest flight price from Chicago to Boston is £43. On average you can expect to pay £175. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £100.

  • Can I find deals for flights from Chicago to Boston that include hotel bookings?

    Yes. In addition to deals on Chicago to Boston flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Boston.

  • Can I find deals for business class flights from Chicago to Boston?

    Yes. Cheapflights offers flight deals from Chicago to Boston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Boston?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Boston (average of £10). Flying from Chicago to Boston in July is currently the most expensive (average of £724). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Burlington
Peabody
Cambridge
Somerville
Quincy
Chelmsford

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Boston

See prices for flight routes from nearby airports that may be better suited for you.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Boston?

Deals for Chicago to Boston flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Boston?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Boston.

Can Cheapflights find flights from Chicago to Boston with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Boston, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Chicago to Boston become cheaper?

Yes! Start tracking prices for Chicago to Boston flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.