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Cheap flights from Chicago to Boston from £47

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 20/8. 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.
CHI — BOS
4 Jun — 11 Jun1
1 adult
Tue 4/6
Tue 11/6

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 Tuesday 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 30 May 2024.

Popular in

June

Cheapest in

January

Round-trip from

£393

One-way from

£116
High demand for flights, 15% potential price rise
Search Deals
Best time to find cheap flights, 25% potential price drop
Search Deals
From Chicago (CHI) to Boston Logan Intl
Search Deals
One-way flight from Chicago (CHI) to Boston Logan Intl
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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 138% 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 42% 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 £272 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.

What is the cheapest time of day to fly from CHI to 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 30% versus a flight in the afternoon.

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 908,271 searches. Data last updated 30 May 2024.
Consider these cheap JetBlue flights we've found departing from Chicago to Boston. Deals update often to give you more flight options matching your criteria
Wed 3/720:33ORD - BOS
Nonstop2h 26mJetBlue
Tue 9/705:14BOS - ORD
1 stop5h 29mJetBlue
Deal found 29/5£115
Tue 20/818:38ORD - BOS
1 stop4h 39mJetBlue
Tue 27/805:14BOS - ORD
1 stop5h 11mJetBlue
Deal found 30/5£122
Tue 16/710:30ORD - BOS
1 stop8h 37mJetBlue
Tue 23/705:14BOS - ORD
1 stop5h 29mJetBlue
Deal found 28/5£123
Fri 14/620:33ORD - BOS
Nonstop2h 26mJetBlue
Mon 17/617:50BOS - ORD
Nonstop2h 57mJetBlue
Deal found 30/5£123
Tue 16/720:33ORD - BOS
Nonstop2h 26mJetBlue
Tue 23/706:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 28/5£124
Mon 1/720:33ORD - BOS
Nonstop2h 26mJetBlue
Wed 10/706:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 29/5£128
Thu 13/610:35ORD - BOS
1 stop8h 32mJetBlue
Sat 15/617:50BOS - ORD
Nonstop2h 57mJetBlue
Deal found 30/5£131
Tue 2/720:33ORD - BOS
Nonstop2h 26mJetBlue
Mon 8/705:14BOS - ORD
1 stop5h 29mJetBlue
Deal found 29/5£135
Sat 15/620:33ORD - BOS
Nonstop2h 26mJetBlue
Thu 20/606:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 28/5£136

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 908,271 searches. Data last updated 30 May 2024.
Browse through some of the cheapest Delta flights travelling from Chicago to Boston. Ensure the flight price, dates, time, and airline match your criteria before you book.
Tue 27/810:30ORD - BOS
Nonstop2h 29mDelta
Tue 27/820:20BOS - ORD
Nonstop2h 58mDelta
Deal found 29/5£108
Fri 21/606:30ORD - BOS
Nonstop2h 28mDelta
Fri 21/619:30BOS - ORD
Nonstop2h 57mDelta
Deal found 29/5£116
Thu 13/606:30ORD - BOS
Nonstop2h 28mDelta
Mon 17/615:55BOS - ORD
Nonstop2h 51mDelta
Deal found 30/5£131
Fri 5/708:00ORD - BOS
Nonstop2h 34mDelta
Fri 12/719:40BOS - ORD
Nonstop2h 59mDelta
Deal found 29/5£132
Tue 11/606:30ORD - BOS
Nonstop2h 28mDelta
Tue 18/607:35BOS - ORD
Nonstop2h 52mDelta
Deal found 28/5£134
Thu 6/620:10ORD - BOS
Nonstop2h 36mDelta
Mon 10/607:35BOS - ORD
Nonstop2h 52mDelta
Deal found 29/5£135
Sat 6/707:00ORD - BOS
Nonstop2h 33mDelta
Wed 17/715:55BOS - ORD
Nonstop3h 01mDelta
Deal found 29/5£139
Tue 16/706:39ORD - BOS
Nonstop2h 26mDelta
Tue 16/719:40BOS - ORD
Nonstop2h 59mDelta
Deal found 29/5£140
Fri 7/606:30ORD - BOS
Nonstop2h 28mDelta
Fri 7/619:30BOS - ORD
Nonstop2h 57mDelta
Deal found 30/5£142

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 908,271 searches. Prices were last updated on 30 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.
Thu 20/610:35ORD - BOS
1 stop8h 32mJetBlue
Mon 24/606:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 30/5£98
Tue 18/620:33ORD - BOS
Nonstop2h 26mJetBlue
Mon 24/606:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 30/5£107
Fri 14/620:33ORD - BOS
Nonstop2h 26mJetBlue
Mon 17/617:50BOS - ORD
Nonstop2h 57mJetBlue
Deal found 30/5£123
Tue 11/620:36ORD - BOS
Nonstop2h 25mAmerican Airlines
Fri 14/605:18BOS - ORD
Nonstop2h 55mAmerican Airlines
Deal found 30/5£126
Sat 8/608:40ORD - BOS
Nonstop2h 29mJetBlue
Sat 8/616:27BOS - ORD
Nonstop2h 55mJetBlue
Deal found 30/5£128
Thu 13/610:35ORD - BOS
1 stop8h 32mJetBlue
Sun 16/606:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 30/5£131
Thu 13/606:30ORD - BOS
Nonstop2h 28mDelta
Mon 17/607:35BOS - ORD
Nonstop2h 52mDelta
Deal found 30/5£131
Wed 5/606:13ORD - BOS
Nonstop2h 26mDelta
Fri 7/619:30BOS - ORD
Nonstop2h 57mDelta
Deal found 29/5£134
Thu 6/620:10ORD - BOS
Nonstop2h 36mDelta
Tue 11/619:30BOS - ORD
Nonstop2h 57mDelta
Deal found 29/5£135

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 908,271 searches. Data last updated 30 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 20/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 27/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£47
Tue 20/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Thu 22/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£57
Tue 20/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 28/815:38BOS - ORD
1 stop5h 57mSpirit Airlines
Deal found 30/5£58
Tue 20/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Sun 25/815:38BOS - ORD
1 stop5h 57mSpirit Airlines
Deal found 30/5£65
Mon 19/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 27/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£72
Tue 20/805:01ORD - BOS
1 stop5h 45mMultiple Airlines
Mon 26/807:00BOS - ORD
Nonstop2h 33mMultiple Airlines
Deal found 30/5£74
Wed 21/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Sun 25/815:38BOS - ORD
1 stop5h 57mSpirit Airlines
Deal found 30/5£78
Mon 19/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Mon 26/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£80
Tue 20/806:00ORD - BOS
1 stop13h 55mSpirit Airlines
Sun 25/815:38BOS - ORD
1 stop5h 57mSpirit Airlines
Deal found 30/5£82

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 908,271 searches. Data last updated 30 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.
Tue 20/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 27/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£47
Tue 20/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Thu 22/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£57
Tue 20/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Sun 25/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£58
Wed 21/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Sun 25/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£65
Mon 19/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 27/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£72
Mon 19/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Mon 26/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£80
Sat 17/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 27/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£87
Mon 19/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Fri 23/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£90
Sat 17/821:04ORD - BOS
Nonstop2h 18mSpirit Airlines
Sat 24/807:00BOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 30/5£94

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 908,271 searches. Data last updated 30 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 8/608:40ORD - BOS
Nonstop2h 29mJetBlue
Sat 8/616:27BOS - ORD
Nonstop2h 55mJetBlue
Deal found 30/5£128
Wed 5/606:13ORD - BOS
Nonstop2h 26mDelta
Fri 7/619:30BOS - ORD
Nonstop2h 57mDelta
Deal found 29/5£134
Thu 6/620:10ORD - BOS
Nonstop2h 36mDelta
Mon 10/607:35BOS - ORD
Nonstop2h 52mDelta
Deal found 29/5£135
Sat 8/617:32ORD - BOS
1 stop5h 50mJetBlue
Thu 13/606:05BOS - ORD
1 stop4h 45mJetBlue
Deal found 29/5£141
Fri 7/606:30ORD - BOS
Nonstop2h 28mDelta
Fri 7/619:30BOS - ORD
Nonstop2h 57mDelta
Deal found 30/5£142
Sat 8/617:32ORD - BOS
1 stop5h 50mJetBlue
Mon 10/605:45BOS - ORD
1 stop5h 12mJetBlue
Deal found 30/5£143
Sat 8/607:00ORD - BOS
Nonstop2h 31mDelta
Sat 8/617:05BOS - ORD
Nonstop2h 58mDelta
Deal found 30/5£149
Fri 7/617:32ORD - BOS
1 stop5h 50mJetBlue
Sat 15/617:50BOS - ORD
Nonstop2h 57mJetBlue
Deal found 30/5£155
Fri 7/617:32ORD - BOS
1 stop5h 50mJetBlue
Mon 10/605:45BOS - ORD
1 stop5h 12mJetBlue
Deal found 30/5£156

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 908,271 searches. Data last updated 30 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 20/618:38ORD - BOS
1 stop4h 40mJetBlue
Deal found 30/5£53
Wed 28/808:40ORD - BOS
Nonstop2h 26mJetBlue
Deal found 30/5£54
Thu 20/610:35ORD - BOS
1 stop8h 32mJetBlue
Deal found 30/5£57
Fri 5/708:00ORD - BOS
Nonstop2h 34mDelta
Deal found 30/5£63
Tue 11/609:00ORD - BOS
Nonstop2h 33mJetBlue
Deal found 30/5£64
Thu 29/806:39ORD - BOS
Nonstop2h 26mDelta
Deal found 29/5£70
Sat 8/617:32ORD - BOS
1 stop5h 50mJetBlue
Deal found 30/5£72
Thu 13/606:30ORD - BOS
Nonstop2h 28mDelta
Deal found 30/5£74
Fri 30/820:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 30/5£75

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 908,271 searches. Data last updated 30 May 2024.

Fly from

Any airport

Fly to

Any airport

Budget

£47 - £154

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 20/8

Nonstop2h 18m

Boston Logan Intl

Tue 27/8

Nonstop2h 33m

£47

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 20/8

Nonstop2h 18m

Boston Logan Intl

Thu 22/8

Nonstop2h 33m

£57

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 20/8

Nonstop2h 18m

Boston Logan Intl

Wed 28/8

1 stop5h 57m

£58

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 20/8

1 stop5h 45m

Boston Logan Intl

Mon 26/8

Nonstop2h 33m

£74

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 20/8

1 stop5h 45m

Boston Logan Intl

Thu 22/8

1 stop5h 09m

£91

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 27/8

Nonstop2h 29m

Boston Logan Intl

Tue 27/8

Nonstop2h 58m

£108

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 3/7

Nonstop2h 26m

Boston Logan Intl

Tue 9/7

1 stop5h 29m

£115

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 11/6

Nonstop2h 25m

Boston Logan Intl

Fri 14/6

Nonstop2h 55m

£126

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 19/8

1 stop4h 26m

Boston Logan Intl

Thu 22/8

1 stop4h 46m

£154

Flights are sorted by cheapest first

Deals found on 30/5

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 24 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

What is the cheapest day 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 26 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

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.

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 30 May 2024.
Read through reviews of airlines operating flights from Chicago to Boston, such as JetBlue, Delta and American Airlines. 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
5,958 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

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
5,958 reviews
Southwest
8.2
Very Good
5,958 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

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

Alaska Airlines
8.1
Very Good
9,201 reviews
Southwest
8.2
Very Good
5,958 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

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

Delta
8.0
Very Good
10,430 reviews
Southwest
8.2
Very Good
5,958 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

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

JetBlue
7.6
Good
4,356 reviews
Southwest
8.2
Very Good
5,958 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

Reviews

1 / 10

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

United Airlines
7.4
Good
10,777 reviews
Southwest
8.2
Very Good
5,958 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

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 £100 on Cheapflights?

    Yes, there are multiple flights from Chicago to Boston for under £100. The cheapest flight booked recently is on Spirit Airlines for just £47, but on average you can expect to pay £84.

  • Are there nonstop flights from Chicago to Boston for under £100 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Boston under £100. A good price for a nonstop flight from Chicago to Boston is less than £103.

  • 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, Thursday, Friday, Saturday.

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

    On average 69 flights depart from Chicago to Boston per day.
    Early Morning (Midnight to 6am) - 4% of flight departures
    Morning (6am - Midday) - 36% of flight departures
    Afternoon (Midday - 6pm) - 39% of flight departures
    Evening (6pm - Midnight) - 20% of flight departures

  • How long is the flight from Chicago to Boston?

    Departing from Chicago to Boston will take you 2h 18m. 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 Spirit Airlines is currently your cheapest option to Boston, with prices starting at £47. Additional return tickets that might be worth considering are offered by Frontier and Delta, with the lowest prices starting at £91 and £108, respectively. You may be able to fly from Chicago to Boston for 77% 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 £53 on JetBlue. Other airlines that offer cheap prices include Delta from £63 and United Airlines 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 £67. On average you can expect to pay £180. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £175.

  • 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 30/5.

  • 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 £500). Flying from Chicago to Boston in July is currently the most expensive (average of £703). 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.

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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.

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Search flights from Chicago to Boston by cabin class

Find flights from Chicago to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from Chicago to Boston

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 30 May 2024.
3%of flight departuresEarly morningMidnight to 6 am
41%of flight departuresMorning6 am to noon
42%of flight departuresAfternoonNoon to 6 pm
14%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Midday
6 PM

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 30 May 2024.
Monday65daily flights
Tuesday57daily flights
Wednesday57daily flights
Thursday60daily flights
Friday58daily flights
Saturday44daily flights
Sunday60daily flights

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Fly with Cheapflights

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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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