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Cheap flights from Chicago to Boston from £45

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 31/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
4 Dec — 11 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in September or January, booked 89 days in advance, depart on a Saturday or Thursday and return on a Thursday

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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 November 2025.

Thu 27/1110:48ORD - BOS
Nonstop2h 20mUnited Airlines
Wed 3/1209:40BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 3/11£89
Thu 4/1207:10ORD - BOS
Nonstop2h 26mDelta
Sun 7/1219:52BOS - ORD
Nonstop2h 55mDelta
Deal found 3/11£90
Wed 26/1120:45ORD - BOS
Nonstop2h 28mJetBlue
Sat 6/1208:30BOS - ORD
Nonstop3h 05mJetBlue
Deal found 3/11£93
Wed 3/1211:25ORD - BOS
Nonstop2h 24mJetBlue
Thu 1/116:31BOS - ORD
Nonstop3h 15mJetBlue
Deal found 2/11£94
Mon 24/1107:10ORD - BOS
Nonstop2h 25mDelta
Wed 3/1216:05BOS - ORD
Nonstop2h 57mDelta
Deal found 3/11£97
Wed 24/1219:41ORD - BOS
Nonstop2h 29mJetBlue
Thu 1/116:31BOS - ORD
Nonstop3h 15mJetBlue
Deal found 3/11£100
Wed 26/1112:50ORD - BOS
Nonstop2h 20mUnited Airlines
Wed 3/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 3/11£100
Wed 3/1211:25ORD - BOS
Nonstop2h 24mJetBlue
Fri 2/116:31BOS - ORD
Nonstop3h 15mJetBlue
Deal found 2/11£101
Sun 21/1221:12ORD - BOS
Nonstop2h 33mUnited Airlines
Sat 10/116:16BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 2/11£102
Sat 6/1211:25ORD - BOS
Nonstop2h 24mJetBlue
Wed 10/1215:40BOS - ORD
1 stop7h 12mJetBlue
Deal found 3/11£103
Thu 4/1213:45ORD - BOS
1 stop7h 30mSouthwest
Sun 7/1205:00BOS - ORD
1 stop8h 15mSouthwest
Deal found 3/11£104
Wed 26/1120:45ORD - BOS
Nonstop2h 28mJetBlue
Wed 3/1215:40BOS - ORD
1 stop7h 12mJetBlue
Deal found 3/11£107

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 November 2025.

Round-trip from

£89

One-way from

£45

Popular in

April

Cheapest in

September

Average price

£175

Good round-trip deal

£484 or less
United Airlines
  • United Airlines
  • 27/11-3/12
  • Nonstop
  • 5h 20m total
  • Chicago to Boston
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United Airlines
  • United Airlines
  • 31/12
  • Nonstop
  • 2h 33m total
  • Chicago to Boston
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (£8 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Boston Logan Intl.
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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 November 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

Thu 27/11

07:45-11:09

Nonstop2h 24m

Boston Logan Intl

Sat 6/12

16:20-18:16

Nonstop2h 56m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 15/11

10:00-13:20

Nonstop2h 20m

Boston Logan Intl

Mon 17/11

15:55-17:55

Nonstop3h 00m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 27/11

07:45-11:09

Nonstop2h 24m

Boston Logan Intl

Thu 4/12

16:05-18:02

Nonstop2h 57m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 24/11

07:10-10:35

Nonstop2h 25m

Boston Logan Intl

Fri 5/12

19:52-21:47

Nonstop2h 55m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 27/11

10:35-14:03

Nonstop2h 28m

Boston Logan Intl

Fri 5/12

19:52-21:47

Nonstop2h 55m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 15/1

08:45-15:50

1 stop6h 05m

Boston Logan Intl

Sat 17/1

15:35-17:44

Nonstop3h 09m

£104

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/12

11:25-14:49

Nonstop2h 24m

Boston Logan Intl

Mon 8/12

15:40-21:52

1 stop7h 12m

£107

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 24/12

19:41-23:10

Nonstop2h 29m

Boston Logan Intl

Fri 2/1

16:31-18:46

Nonstop3h 15m

£107

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 24/1

08:45-15:50

1 stop6h 05m

Boston Logan Intl

Sun 25/1

15:35-17:44

Nonstop3h 09m

£110

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 26/11

19:15-22:45

Nonstop2h 30m

Boston Logan Intl

Thu 4/12

16:05-18:02

Nonstop2h 57m

£112

Flights are sorted by cheapest return flights first.

Deals found on 3/11

Showing 1-10 of 24 results
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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 31 October 2025.

Booking 89 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, November is the cheapest month in which you can book a flight from Chicago to Boston (average of £54). Flying from Chicago to Boston in February is currently the most expensive (average of £104). 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 November 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 in the evening, which can drop the price by up to 72% versus a flight at midday.

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 November 2025.

The most flights from CHI to BOS are scheduled on a Monday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 on average).

How much does it cost for a return flight from Chicago to Boston?

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 49 inbound flights from Chicago per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • How long is the flight from Chicago to Boston?

    Departing from Chicago to Boston will take you 2h 20m. Chicago and Boston are separated by a distance of 864 mi. Generally, flights for this route are direct.

  • 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 £45 on United Airlines. Other airlines that offer cheap prices include Delta from £45 and JetBlue from £45 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 Envoy Air (81%), Etihad Airways (72%) or Virgin Atlantic (71%) 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 £276. On average you can expect to pay £682. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £105.

  • 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, November is the cheapest month in which you can book a flight from Chicago to Boston (average of £54). Flying from Chicago to Boston in February is currently the most expensive (average of £104). 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 Boston?

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

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Alternative routes for Chicago to Boston

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Boston flights

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.

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