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Cheap flights from Chicago to Boston from £54

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 30/5. 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.
CHI — BOS
21 May — 28 May1
1 adult
Tue 21/5
Tue 28/5

The best prices from Chicago to Boston Logan Intl are usually found in January or February, booked 84 days in advance, depart on a Friday or Thursday and return on a Tuesday

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 16 May 2024.

Popular in

June

Cheapest in

January

Round-trip from

£395

One-way from

£133
High demand for flights, 17% potential price rise
Best time to find cheap flights, 25% potential price drop
From Chicago (CHI) to Boston Logan Intl
One-way flight from Chicago (CHI) to Boston Logan Intl

What is the cheapest day to fly round-trip from Chicago to Boston?

Departing on a Friday is a good option for securing a great price. You can expect to save up to 136% when planning your travel around this day of the week.

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

Travelers have found it’s best to book a flight 51 days in advance to save up to 46% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 51 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Boston 1-2 weeks in advance for as low as £207, or £273 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago to Boston?

Flights from Chicago to Boston lean towards being more expensive in June. Prices are generally better when you fly from Chicago to Boston in January, with the cheapest ticket starting at £78.

When is the cheapest time to fly from Chicago to Boston (CHI - BOS)?

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 48% versus a flight in the afternoon.

Cheap Delta flights from Chicago to Boston

Explore cheap flight options specifically provided by Delta for the route between Chicago and Boston. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 844,321 searches. Data last updated 16 May 2024.
Consider these cheap Delta flights we've found departing from Chicago to Boston. Deals update often to give you more flight options matching your criteria
Fri 31/520:10ORD - BOS
Nonstop2h 36mDelta
Wed 5/606:25BOS - ORD
Nonstop2h 55mDelta
Deal found 14/5£108
Sat 8/617:52ORD - BOS
Nonstop2h 40mDelta
Wed 12/607:35BOS - ORD
Nonstop2h 52mDelta
Deal found 14/5£116
Sat 8/617:52ORD - BOS
Nonstop2h 40mDelta
Thu 13/607:35BOS - ORD
Nonstop2h 52mDelta
Deal found 14/5£140
Fri 31/520:10ORD - BOS
Nonstop2h 36mDelta
Sat 1/616:25BOS - ORD
Nonstop2h 51mDelta
Deal found 16/5£144
Sun 21/706:35ORD - BOS
Nonstop2h 26mDelta
Tue 23/719:40BOS - ORD
Nonstop2h 59mDelta
Deal found 15/5£163
Sat 26/1008:00ORD - BOS
Nonstop2h 28mDelta
Sat 26/1017:40BOS - ORD
Nonstop2h 49mDelta
Deal found 16/5£165
Tue 28/520:10ORD - BOS
Nonstop2h 36mDelta
Tue 4/614:00BOS - ORD
Nonstop2h 50mDelta
Deal found 16/5£168
Fri 24/520:10ORD - BOS
Nonstop2h 36mDelta
Mon 27/506:25BOS - ORD
Nonstop2h 55mDelta
Deal found 16/5£171
Fri 5/708:00ORD - BOS
Nonstop2h 34mDelta
Fri 12/707:20BOS - ORD
Nonstop2h 59mDelta
Deal found 15/5£175

Cheap JetBlue flights from Chicago to Boston

Explore cheap flight options specifically provided by JetBlue for the route between Chicago and Boston. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 844,321 searches. Data last updated 16 May 2024.
Browse through some of the cheapest JetBlue flights travelling from Chicago to Boston. Ensure the flight price, dates, time, and airline match your criteria before you book.
Wed 21/808:29ORD - BOS
Nonstop2h 26mJetBlue
Sun 1/906:12BOS - ORD
1 stop4h 39mJetBlue
Deal found 15/5£115
Tue 20/810:37ORD - BOS
1 stop8h 25mJetBlue
Sun 1/906:12BOS - ORD
1 stop4h 39mJetBlue
Deal found 16/5£123
Thu 30/508:40ORD - BOS
Nonstop2h 29mJetBlue
Mon 3/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/5£129
Wed 29/519:15ORD - BOS
Nonstop2h 26mJetBlue
Thu 30/506:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£132
Sat 24/819:20ORD - BOS
Nonstop2h 25mJetBlue
Mon 2/906:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£136
Tue 25/610:35ORD - BOS
1 stop8h 32mJetBlue
Sun 30/606:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/5£139
Thu 8/810:37ORD - BOS
1 stop8h 25mJetBlue
Tue 13/805:15BOS - ORD
1 stop5h 36mJetBlue
Deal found 15/5£144
Tue 6/810:37ORD - BOS
1 stop8h 25mJetBlue
Tue 13/810:06BOS - ORD
1 stop7h 24mJetBlue
Deal found 16/5£147
Fri 30/819:20ORD - BOS
Nonstop2h 25mJetBlue
Tue 3/906:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£148

Cheap Chicago to Boston flights in May & June 2024

Find cheap flight options from Chicago to Boston specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 844,321 searches. Prices were last updated on 16 May 2024.
These are some of the best deals we've found on flights to Boston in 2024 at this time. If these deals don't appeal to you, be sure to come back soon for more options.
Tue 4/621:25ORD - BOS
1 stop16h 24mSpirit Airlines
Wed 5/621:25BOS - ORD
1 stop17h 15mSpirit Airlines
Deal found 16/5£127
Thu 30/508:40ORD - BOS
Nonstop2h 29mJetBlue
Sat 1/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£129
Sat 25/519:15ORD - BOS
Nonstop2h 26mJetBlue
Thu 30/506:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£132
Tue 25/610:35ORD - BOS
1 stop8h 32mJetBlue
Sun 30/606:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/5£139
Thu 30/508:40ORD - BOS
Nonstop2h 29mJetBlue
Sun 2/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£140
Fri 31/520:10ORD - BOS
Nonstop2h 36mDelta
Sat 1/616:25BOS - ORD
Nonstop2h 51mDelta
Deal found 16/5£144
Wed 29/508:40ORD - BOS
Nonstop2h 29mJetBlue
Mon 3/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£148
Sun 26/508:40ORD - BOS
Nonstop2h 29mJetBlue
Thu 30/506:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/5£148
Wed 29/519:15ORD - BOS
Nonstop2h 26mJetBlue
Mon 3/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/5£149

Chicago to Boston 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Boston in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 844,321 searches. Data last updated 16 May 2024.
These are some of the best deals we've found on flights to Boston in 2024 at this time. If these deals don't appeal to you, be sure to come back soon for more options.
Wed 7/810:37ORD - BOS
1 stop8h 25mJetBlue
Tue 13/806:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£115
Wed 7/817:15ORD - BOS
1 stop5h 11mJetBlue
Tue 13/806:12BOS - ORD
1 stop4h 39mJetBlue
Deal found 16/5£123
Tue 4/621:25ORD - BOS
1 stop16h 24mSpirit Airlines
Wed 5/621:25BOS - ORD
1 stop17h 15mSpirit Airlines
Deal found 16/5£127
Thu 30/508:40ORD - BOS
Nonstop2h 29mJetBlue
Sat 1/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£129
Sat 25/519:15ORD - BOS
Nonstop2h 26mJetBlue
Thu 30/506:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£132
Sat 24/819:20ORD - BOS
Nonstop2h 25mJetBlue
Mon 2/906:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£136
Tue 25/610:35ORD - BOS
1 stop8h 32mJetBlue
Sun 30/606:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/5£139
Thu 30/508:40ORD - BOS
Nonstop2h 29mJetBlue
Sun 2/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£140
Wed 18/906:30ORD - BOS
Nonstop2h 28mDelta
Wed 18/919:40BOS - ORD
Nonstop2h 54mDelta
Deal found 16/5£141

Direct flights to Boston from Chicago

Discover direct flight options from Chicago to Boston. Find direct flights with no stopovers, providing a convenient travel experience. Explore direct flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 844,321 searches. Data last updated 16 May 2024.
Consider booking one of these non-stop flights heading from Chicago to Boston. Select from other flights from Chicago to Boston by using the search form above.
Thu 30/508:40ORD - BOS
Nonstop2h 29mJetBlue
Sat 1/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£129
Wed 29/519:15ORD - BOS
Nonstop2h 26mJetBlue
Thu 30/506:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£132
Sat 24/819:20ORD - BOS
Nonstop2h 25mJetBlue
Mon 2/906:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£136
Wed 18/906:30ORD - BOS
Nonstop2h 28mDelta
Wed 18/919:40BOS - ORD
Nonstop2h 54mDelta
Deal found 16/5£141
Fri 31/520:10ORD - BOS
Nonstop2h 36mDelta
Sat 1/616:25BOS - ORD
Nonstop2h 51mDelta
Deal found 16/5£144
Sun 26/508:40ORD - BOS
Nonstop2h 29mJetBlue
Thu 30/506:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/5£148
Wed 29/519:15ORD - BOS
Nonstop2h 26mJetBlue
Mon 3/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/5£149
Sat 1/608:40ORD - BOS
Nonstop2h 29mJetBlue
Wed 5/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£152
Tue 28/520:10ORD - BOS
Nonstop2h 36mDelta
Tue 4/616:43BOS - ORD
Nonstop3h 02mDelta
Deal found 16/5£155

Chicago to Boston flights leaving soon

Find last-minute flight options from Chicago to Boston for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 844,321 searches. Data last updated 16 May 2024.
Have a look at some of the last-minute flights available departing from Chicago to Boston. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Sat 25/519:15ORD - BOS
Nonstop2h 26mJetBlue
Thu 30/506:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£132
Sun 26/508:40ORD - BOS
Nonstop2h 29mJetBlue
Thu 30/506:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/5£148
Sat 25/519:15ORD - BOS
Nonstop2h 26mJetBlue
Wed 29/516:25BOS - ORD
Nonstop2h 55mJetBlue
Deal found 15/5£152
Sat 25/519:15ORD - BOS
Nonstop2h 26mJetBlue
Wed 29/516:25BOS - ORD
Nonstop2h 55mJetBlue
Deal found 16/5£155
Sun 26/508:40ORD - BOS
Nonstop2h 29mJetBlue
Wed 29/516:25BOS - ORD
Nonstop2h 55mJetBlue
Deal found 15/5£169
Fri 24/520:10ORD - BOS
Nonstop2h 36mDelta
Mon 27/506:25BOS - ORD
Nonstop2h 55mDelta
Deal found 16/5£171
Sun 26/508:40ORD - BOS
Nonstop2h 29mJetBlue
Fri 7/616:25BOS - ORD
Nonstop2h 55mJetBlue
Deal found 16/5£179
Sun 26/508:02ORD - BOS
Nonstop2h 33mDelta
Thu 6/616:43BOS - ORD
Nonstop3h 02mDelta
Deal found 16/5£183
Fri 24/519:15ORD - BOS
Nonstop2h 26mJetBlue
Wed 29/506:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 16/5£188

One-way flights to Boston from Chicago

Search for one-way flight options from Chicago to Boston. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 844,321 searches. Data last updated 16 May 2024.
If you're seeking multiple options on one-way flights from Chicago to Boston, be sure to check out these deals, which are updated often. Those needing a return flight from Chicago to Boston can use the search form above.
Thu 30/508:40ORD - BOS
Nonstop2h 29mJetBlue
Deal found 16/5£54
Wed 7/817:15ORD - BOS
1 stop5h 11mJetBlue
Deal found 16/5£62
Tue 9/710:37ORD - BOS
1 stop8h 25mJetBlue
Deal found 16/5£66
Fri 28/621:10ORD - BOS
Nonstop2h 35mUnited Airlines
Deal found 16/5£75
Wed 29/519:15ORD - BOS
Nonstop2h 26mJetBlue
Deal found 16/5£78
Fri 19/717:15ORD - BOS
1 stop6h 02mJetBlue
Deal found 16/5£82
Thu 31/1017:27ORD - BOS
Nonstop2h 24mDelta
Deal found 16/5£83
Sat 13/710:37ORD - BOS
1 stop8h 25mJetBlue
Deal found 16/5£90
Thu 10/1018:05ORD - BOS
1 stop5h 13mJetBlue
Deal found 15/5£94

Find flights from Chicago to Boston within your budget

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 844,321 searches. Data last updated 16 May 2024.

Fly from

Any airport

Fly to

Any airport

Budget

£108 - £200

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 31/5

Nonstop2h 36m

Boston Logan Intl

Wed 5/6

Nonstop2h 55m

£108

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 21/8

Nonstop2h 26m

Boston Logan Intl

Sun 1/9

1 stop4h 39m

£115

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/6

Nonstop2h 40m

Boston Logan Intl

Wed 12/6

Nonstop2h 52m

£116

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/6

1 stop11h 49m

Boston Logan Intl

Wed 5/6

1 stop12h 38m

£117

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 20/8

1 stop8h 25m

Boston Logan Intl

Sun 1/9

1 stop4h 39m

£123

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 30/5

Nonstop2h 29m

Boston Logan Intl

Mon 3/6

Nonstop2h 54m

£129

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/6

Nonstop2h 40m

Boston Logan Intl

Thu 13/6

Nonstop2h 52m

£140

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 29/5

1 stop8h 40m

Boston Logan Intl

Thu 30/5

1 stop7h 50m

£193

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 28/5

Nonstop2h 20m

Boston Logan Intl

Thu 30/5

Nonstop2h 50m

£200

Flights are sorted by cheapest first

Deals found on 14/5

When is the best time to 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 10 May 2024.
Booking 84 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.
Search Deals

When is the cheapest time to fly from Chicago to Boston?

Use this chart to determine the cheapest time to fly return from Chicago to Boston. Price data was last updated on 12 May 2024.
Morning
Midday
Afternoon
Evening
All times are departure.
Travellers seeking maximum savings on their Chicago to Boston flight should consider departing on Tuesday mornings when fares are most often at their lowest. Thursday at midday flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Boston by month

Plan your trip from Chicago to Boston by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago to Boston is currently £76 while a return flight costs £138. Price data was last updated on 12 May 2024.

Currently, November is the cheapest month in which you can book a flight from Chicago to Boston (average of £501). Flying from Chicago to Boston in July is currently the most expensive (average of £694). 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.

January

£409

February

£407

March

£399

April

£418

May

£424

June

£512

July

£548

August

£480

September

£439

October

£424

November

£395

December

£397

Temperature and rainfall in Boston by month

Plan your trip to Boston by taking into account the average temperature and rainfall totals by month.

BOS

Temperature

-1 - 23 °C

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 16 May 2024.
Read through reviews of airlines operating flights from Chicago to Boston, such as Delta, JetBlue and Southwest. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very Good
6,039 reviews

Overall

8.2

Comfort

8.1

Entertainment

7.8

Food

7.3

Crew

8.7

Boarding

8.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very Good
6,039 reviews
Southwest
8.2
Very Good
6,039 reviews

Overall

8.2

Comfort

8.1

Entertainment

7.8

Food

7.3

Crew

8.7

Boarding

8.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

8.1
Very Good
9,157 reviews
Southwest
8.2
Very Good
6,039 reviews

Overall

8.2

Comfort

8.1

Entertainment

7.8

Food

7.3

Crew

8.7

Boarding

8.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

8.0
Very Good
10,673 reviews
Southwest
8.2
Very Good
6,039 reviews

Overall

8.2

Comfort

8.1

Entertainment

7.8

Food

7.3

Crew

8.7

Boarding

8.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

7.6
Good
4,472 reviews
Southwest
8.2
Very Good
6,039 reviews

Overall

8.2

Comfort

8.1

Entertainment

7.8

Food

7.3

Crew

8.7

Boarding

8.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

7.4
Good
10,924 reviews
Southwest
8.2
Very Good
6,039 reviews

Overall

8.2

Comfort

8.1

Entertainment

7.8

Food

7.3

Crew

8.7

Boarding

8.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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

  • Can I find flights from Chicago to Boston for under £200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Boston for under £200. The cheapest flight booked recently is on Delta for just £108, but on average you can expect to pay £137.

  • Are there nonstop flights from Chicago to Boston for under £200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Boston under £200. A good price for a nonstop flight from Chicago to Boston is less than £162.

  • Are there last-minute flights available from Chicago to Boston for under £200?

    There are currently 20+ open flights from Chicago to Boston within the next 7 days for less than £200.

  • What days are direct flights available from Chicago to Boston?

    Direct flights are available for this route on the following days: Sunday, Monday, Tuesday, Friday, Saturday.

  • How many flights depart from Chicago to Boston on average per day?

    On average 16 flights depart from Chicago to Boston per day.
    Morning (6am - Midday) - 19% of flight departures
    Afternoon (Midday - 6pm) - 25% of flight departures
    Evening (6pm - Midnight) - 56% of flight departures

  • How long is the flight from Chicago to Boston?

    Departing from Chicago to Boston will take you 2h 26m. Chicago and Boston are separated by a distance of 869 mi. Both multi-stop and direct flights can be found to your destination and back.

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

    Flying on Delta is currently your cheapest option to Boston, with prices starting at £108. Additional return tickets that might be worth considering are offered by JetBlue and Spirit Airlines, with the lowest prices starting at £115 and £117, respectively. You may be able to fly from Chicago to Boston for 49% 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 £54 on JetBlue. Other airlines that offer cheap prices include United Airlines from £75 and Delta from £83 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 Republic Airways (93%), Envoy Air (91%) or EL AL (89%) 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 £57. On average you can expect to pay £162. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £152.

  • What does ORD to BOS mean?

    Great question - ORD to BOS just means Chicago O'Hare Intl Airport to Boston Logan Intl Airport. Now you’ll know what these unique codes when you look for flights! Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Chicago to Boston that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Boston flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Boston with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Boston flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Boston that allow pets onboard?

    Many airlines flying from Chicago to Boston offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Boston?

    Yes, you can often find last-minute deals on Chicago to Boston flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Boston flight deals updated?

    The Chicago to Boston flight deals you see on this page were last updated on 16/5.

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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.