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Cheap flights from Boston to Chicago 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 3/9. 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.
BOS — CHI
6 Jun — 13 Jun1
1 adult
Thu 6/6
Thu 13/6

The best prices from Boston Logan Intl to Chicago are usually found in January or February, booked 65 days in advance, depart on a Tuesday or Monday and return on a Friday

Cheap flight deals from Boston to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Chicago (CHI). 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 1 June 2024.

Popular in

June

Cheapest in

January

Round-trip from

£435

One-way from

£96
High demand for flights, 16% potential price rise
Search Deals
Best time to find cheap flights, 31% potential price drop
Search Deals
From Boston Logan Intl to Chicago (CHI)
Search Deals
One-way flight from Boston Logan Intl to Chicago (CHI)
Search Deals

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

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

Travelers have found it’s best to book a flight 52 days in advance to save up to 38% 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 52 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 Boston to Chicago 1-2 weeks in advance for as low as £219, or £258 for flights within the next 24 hours.

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

Flights from Boston to Chicago lean towards being more expensive in June. Prices are generally better when you fly from Boston to Chicago in January, with the cheapest ticket starting at £83.

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

When flying from Boston to Chicago, 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 26% versus a flight in the morning.

Cheap United Airlines flights from Boston to Chicago

Explore cheap flight options specifically provided by United Airlines for the route between Boston and Chicago. 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 1 June 2024.
Take a look at some of the lowest-priced United Airlines flights heading from Boston to Chicago. Make sure to double check the flight details before booking.
Tue 23/709:30BOS - ORD
1 stop7h 43mUnited Airlines
Thu 25/721:10ORD - BOS
Nonstop2h 35mUnited Airlines
Deal found 1/6£194
Mon 17/619:10BOS - ORD
1 stop5h 10mUnited Airlines
Tue 18/607:10ORD - BOS
1 stop5h 05mUnited Airlines
Deal found 31/5£219
Tue 23/705:30BOS - ORD
1 stop7h 10mUnited Airlines
Thu 25/716:00ORD - BOS
1 stop6h 58mUnited Airlines
Deal found 1/6£229
Mon 17/619:10BOS - ORD
1 stop5h 10mUnited Airlines
Tue 18/621:32ORD - BOS
2 stops11h 32mUnited Airlines
Deal found 31/5£269

Cheap JetBlue flights from Boston to Chicago

Explore cheap flight options specifically provided by JetBlue for the route between Boston and Chicago. 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 1 June 2024.
Have a look at some of the cheapest available JetBlue flights departing from Boston and landing in Chicago. Check back soon if you're not seeing flights that suit your needs.
Mon 17/617:50BOS - ORD
Nonstop2h 57mJetBlue
Tue 25/620:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£107
Tue 9/705:14BOS - ORD
1 stop5h 29mJetBlue
Wed 17/720:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£115
Mon 1/717:50BOS - ORD
Nonstop2h 57mJetBlue
Tue 9/720:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£116
Sat 17/805:14BOS - ORD
1 stop5h 11mJetBlue
Tue 20/818:38ORD - BOS
1 stop4h 39mJetBlue
Deal found 31/5£123
Wed 12/606:10BOS - ORD
Nonstop2h 54mJetBlue
Tue 18/620:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£126
Wed 10/706:00BOS - ORD
Nonstop2h 54mJetBlue
Mon 15/720:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£127
Tue 11/606:10BOS - ORD
Nonstop2h 54mJetBlue
Wed 12/609:00ORD - BOS
Nonstop2h 33mJetBlue
Deal found 1/6£128
Fri 16/805:14BOS - ORD
1 stop5h 11mJetBlue
Wed 21/808:40ORD - BOS
Nonstop2h 26mJetBlue
Deal found 30/5£130
Wed 3/705:14BOS - ORD
1 stop5h 36mJetBlue
Tue 9/720:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£131

Cheap Boston to Chicago flights in June & July 2024

Find cheap flight options from Boston to Chicago specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 908,271 searches. Prices were last updated on 1 June 2024.
These are some of the most attractive deals on flights from Boston to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Mon 17/617:50BOS - ORD
Nonstop2h 57mJetBlue
Tue 25/620:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£107
Tue 18/619:30BOS - ORD
Nonstop2h 57mDelta
Wed 26/606:30ORD - BOS
Nonstop2h 28mDelta
Deal found 31/5£115
Sat 15/617:50BOS - ORD
Nonstop2h 57mJetBlue
Wed 21/810:10ORD - BOS
1 stop8h 22mJetBlue
Deal found 31/5£123
Wed 19/619:30BOS - ORD
Nonstop2h 57mDelta
Tue 27/813:59ORD - BOS
Nonstop2h 42mDelta
Deal found 31/5£123
Wed 12/606:10BOS - ORD
Nonstop2h 54mJetBlue
Tue 18/620:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£126
Tue 11/606:10BOS - ORD
Nonstop2h 54mJetBlue
Wed 12/619:15ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£127
Tue 11/606:10BOS - ORD
Nonstop2h 54mJetBlue
Wed 12/609:00ORD - BOS
Nonstop2h 33mJetBlue
Deal found 1/6£128
Sat 15/617:50BOS - ORD
Nonstop2h 57mJetBlue
Thu 22/808:40ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£131
Tue 11/606:10BOS - ORD
Nonstop2h 54mJetBlue
Wed 12/610:43ORD - BOS
1 stop5h 57mJetBlue
Deal found 31/5£134

Boston to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Boston and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 908,271 searches. Data last updated 1 June 2024.
These are some of the most attractive deals on flights from Boston to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Mon 17/617:50BOS - ORD
Nonstop2h 57mJetBlue
Tue 25/620:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£107
Tue 2/706:00BOS - ORD
Nonstop2h 54mJetBlue
Tue 9/720:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£108
Fri 12/706:35BOS - ORD
Nonstop2h 54mSpirit Airlines
Sun 14/721:59ORD - BOS
1 stop10h 37mSpirit Airlines
Deal found 31/5£113
Tue 9/705:14BOS - ORD
1 stop5h 29mJetBlue
Wed 17/720:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£115
Tue 18/619:30BOS - ORD
Nonstop2h 57mDelta
Wed 26/606:30ORD - BOS
Nonstop2h 28mDelta
Deal found 31/5£115
Mon 1/717:50BOS - ORD
Nonstop2h 57mJetBlue
Tue 9/720:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£116
Fri 12/710:26BOS - ORD
1 stop11h 32mSpirit Airlines
Sun 14/721:59ORD - BOS
1 stop10h 37mSpirit Airlines
Deal found 31/5£119
Sat 17/805:14BOS - ORD
1 stop5h 11mJetBlue
Tue 20/818:38ORD - BOS
1 stop4h 39mJetBlue
Deal found 31/5£123
Tue 2/717:05BOS - ORD
Nonstop2h 57mDelta
Mon 8/706:39ORD - BOS
Nonstop2h 26mDelta
Deal found 31/5£123

Direct flights to Chicago from Boston

Discover direct flight options from Boston to Chicago. 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 1 June 2024.
For a quicker trip, book one of these direct flights from Boston to Chicago. Search for alternative flights from Boston to Chicago by utilising the search form above.
Mon 17/617:50BOS - ORD
Nonstop2h 57mJetBlue
Tue 25/620:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£107
Tue 2/706:00BOS - ORD
Nonstop2h 54mJetBlue
Tue 9/720:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£108
Tue 18/619:30BOS - ORD
Nonstop2h 57mDelta
Wed 26/606:30ORD - BOS
Nonstop2h 28mDelta
Deal found 31/5£115
Mon 1/717:50BOS - ORD
Nonstop2h 57mJetBlue
Tue 9/720:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£116
Mon 19/806:00BOS - ORD
Nonstop2h 54mJetBlue
Tue 20/820:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 30/5£123
Tue 2/717:05BOS - ORD
Nonstop2h 57mDelta
Fri 5/708:00ORD - BOS
Nonstop2h 34mDelta
Deal found 31/5£124
Wed 12/606:10BOS - ORD
Nonstop2h 54mJetBlue
Tue 18/620:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£126
Wed 10/706:00BOS - ORD
Nonstop2h 54mJetBlue
Mon 26/820:33ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£127
Sat 15/617:50BOS - ORD
Nonstop2h 57mJetBlue
Thu 22/808:40ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£131

Boston to Chicago flights leaving soon

Find last-minute flight options from Boston to Chicago 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 1 June 2024.
Users seeking a last-minute flight from Boston to Chicago should consider booking one of these fares. Tip: verify your flight details before completing your reservation.
Thu 6/619:59BOS - ORD
Nonstop2h 53mDelta
Sat 8/617:52ORD - BOS
Nonstop2h 40mDelta
Deal found 31/5£149
Mon 10/605:45BOS - ORD
1 stop5h 12mJetBlue
Thu 13/610:35ORD - BOS
1 stop8h 32mJetBlue
Deal found 31/5£152
Wed 5/606:10BOS - ORD
Nonstop2h 54mJetBlue
Sat 8/608:40ORD - BOS
Nonstop2h 29mJetBlue
Deal found 31/5£196
Wed 5/606:10BOS - ORD
Nonstop2h 54mJetBlue
Fri 7/617:32ORD - BOS
1 stop5h 50mJetBlue
Deal found 31/5£203
Wed 5/610:03BOS - ORD
1 stop7h 42mJetBlue
Fri 7/617:32ORD - BOS
1 stop5h 50mJetBlue
Deal found 31/5£211
Fri 7/619:30BOS - ORD
Nonstop2h 57mDelta
Wed 12/606:30ORD - BOS
Nonstop2h 28mDelta
Deal found 31/5£247
Fri 7/610:08BOS - ORD
1 stop7h 38mJetBlue
Wed 12/619:15ORD - BOS
Nonstop2h 26mJetBlue
Deal found 31/5£259
Wed 5/606:10BOS - ORD
Nonstop2h 54mJetBlue
Wed 5/610:45ORD - BOS
1 stop5h 54mJetBlue
Deal found 31/5£268
Thu 6/606:10BOS - ORD
Nonstop2h 54mJetBlue
Thu 6/617:32ORD - BOS
1 stop5h 50mJetBlue
Deal found 31/5£272

One-way flights to Chicago from Boston

Search for one-way flight options from Boston to Chicago. 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 1 June 2024.
Some of the best available deals we've found on one-way flights from Boston to Chicago. Users in need of a round-trip flight from Boston to Chicago instead should update the search form at the top of page.
Tue 3/917:50BOS - ORD
Nonstop2h 57mJetBlue
Deal found 1/6£54
Sat 31/805:14BOS - ORD
1 stop5h 11mJetBlue
Deal found 1/6£61
Sat 15/617:50BOS - ORD
Nonstop2h 57mJetBlue
Deal found 31/5£62
Tue 11/619:30BOS - ORD
Nonstop2h 57mDelta
Deal found 31/5£64
Mon 17/619:30BOS - ORD
Nonstop2h 57mDelta
Deal found 31/5£65
Fri 5/711:44BOS - ORD
1 stop6h 59mJetBlue
Deal found 31/5£70
Thu 13/606:05BOS - ORD
1 stop4h 45mJetBlue
Deal found 31/5£71
Thu 13/606:00BOS - ORD
Nonstop2h 54mJetBlue
Deal found 30/5£74
Fri 30/811:30BOS - ORD
1 stop7h 13mJetBlue
Deal found 1/6£77

Find flights from Boston to Chicago within your budget

Customise your flight search to find flights from Boston to Chicago 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 1 June 2024.

Fly from

Any airport

Fly to

Any airport

Budget

£107 - £231

Route

Depart

Return

Price

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Mon 17/6

Nonstop2h 57m

Chicago O'Hare Intl

Tue 25/6

Nonstop2h 26m

£107

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/7

Nonstop2h 54m

Chicago O'Hare Intl

Tue 9/7

Nonstop2h 26m

£108

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/7

Nonstop2h 54m

Chicago O'Hare Intl

Sun 14/7

1 stop10h 37m

£113

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 18/6

Nonstop2h 57m

Chicago O'Hare Intl

Wed 26/6

Nonstop2h 28m

£115

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 23/7

1 stop5h 44m

Chicago O'Hare Intl

Thu 25/7

1 stop12h 14m

£132

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 23/7

Nonstop2h 56m

Chicago O'Hare Intl

Thu 25/7

Nonstop2h 27m

£159

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 23/7

1 stop7h 43m

Chicago O'Hare Intl

Thu 25/7

Nonstop2h 35m

£194

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/7

1 stop24h 37m

Chicago O'Hare Intl

Sun 14/7

1 stop13h 55m

£225

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Mon 17/6

1 stop8h 25m

Chicago O'Hare Intl

Tue 18/6

2 stops12h 45m

£231

Flights are sorted by cheapest first

Deals found on 31/5

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

Use this chart to determine the optimal time to book a return flight from Boston to Chicago. Price data was last updated on 24 May 2024.
The best time to book flights from Boston to Chicago is 65 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Search Deals

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

Use this chart to determine the cheapest time to fly return from Boston to Chicago. Price data was last updated on 26 May 2024.
Morning
Midday
Afternoon
Evening
All times are departure.
Travellers seeking maximum savings on their Boston to Chicago flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Thursday mornings 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 Boston to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Boston 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 Chicago by month

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

CHI

Temperature

-5 - 23 °C

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 1 June 2024.
Read reviews from past customers who have flown United Airlines, JetBlue and Delta from Boston to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very Good
5,952 reviews
Check prices

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Boarding

8.3

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
5,952 reviews
Southwest
8.2
Very Good
5,952 reviews
Check prices

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Boarding

8.3

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
9,197 reviews
Southwest
8.2
Very Good
5,952 reviews
Check prices

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Boarding

8.3

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
10,419 reviews
Southwest
8.2
Very Good
5,952 reviews
Check prices

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Boarding

8.3

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
4,351 reviews
Southwest
8.2
Very Good
5,952 reviews
Check prices

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Boarding

8.3

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
10,754 reviews
Southwest
8.2
Very Good
5,952 reviews
Check prices

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Boarding

8.3

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 Boston to Chicago. 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 from for flights from Boston to Chicago?

    Boston Logan Intl (BOS) is the airport you will fly out of if you book a flight from Boston to Chicago. You should not have trouble finding flights to Chicago from Logan Intl; the airport handles an average of 51 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Boston airport to Chicago. It is only a 2.6 mi journey to Logan Intl (BOS) from Boston’s city center.

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

    Yes, there are multiple flights from Boston to Chicago for under £200. The cheapest flight booked recently is on JetBlue for just £107, but on average you can expect to pay £123.

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

    Cheapflights has at least 20 direct flights from Boston to Chicago under £200. A good price for a nonstop flight from Boston to Chicago is less than £131.

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

    There are currently 14+ open flights from Boston to Chicago within the next 7 days for less than £200.

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

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

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

    71 flight departures from Boston to Chicago per day on average.
    Early Morning (Midnight to 6am) - 20% of flight departures
    Morning (6am - Midday) - 30% of flight departures
    Afternoon (Midday - 6pm) - 30% of flight departures
    Evening (6pm - Midnight) - 21% of flight departures

  • How long is the flight from Boston to Chicago?

    A quick flight from Boston to Chicago can take about 2h 54m. JetBlue provides one of the quickest options available for as low as £107. Airlines will cover a distance of 869 mi. All flights are typically direct.

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

    Currently priced at £107, JetBlue will fly you from Boston to Chicago and back. In addition to JetBlue, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Spirit Airlines and Delta - these airlines can fly you to your destination from £113 and £115, respectively. These flights start at 49% lower than the current average price 3 months from now.

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

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as £54. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Boston to Chicago for a low price.

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

    No one likes to see their flight delayed. When booking a flight from Boston to Chicago consider choosing Scandinavian Airlines (97%), ANA (96%) or Japan Airlines (96%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is £39. On average you can expect to pay £204. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £113.

  • What does BOS to ORD mean?

    This is defined as Boston Logan Intl Airport (BOS) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

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

    The amount of baggage you can bring on your Boston to Chicago 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 Boston to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Boston to Chicago 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 Boston to Chicago that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Boston to Chicago 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 Boston to Chicago that allow pets onboard?

    Many airlines flying from Boston to Chicago 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 Boston to Chicago?

    Yes, you can often find last-minute deals on Boston to Chicago 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 Boston to Chicago flight deals updated?

    The Boston to Chicago flight deals you see on this page were last updated on 31/5.

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

    Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £601). Flying from Boston to Chicago in July is currently the most expensive (average of £766). 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

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 Boston to Chicago
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Boston to Charleston flights

Search flights from Boston to Chicago by cabin class

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

Find hourly flight availability from Boston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 1 June 2024.
7%of flight departuresEarly morningMidnight to 6 am
38%of flight departuresMorning6 am to noon
51%of flight departuresAfternoonNoon to 6 pm
4%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Midday
6 PM

Weekly flight availability from Boston to Chicago

Explore weekly flight availability from Boston to Chicago. 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 1 June 2024.
Monday66daily flights
Tuesday46daily flights
Wednesday52daily flights
Thursday56daily flights
Friday61daily flights
Saturday31daily flights
Sunday51daily flights

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Fly with Cheapflights

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

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Boston today with Cheapflights!

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

Cheapflights helps you find that perfect flight to Chicago from Boston by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to Chicago flexibly with Cheapflights today.

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

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Boston today and book when prices fit your budget.

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