Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Boston to Chicago from £27

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 12/6. 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
20 May — 27 May1
1 adult
Mon 20/5
Mon 27/5

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 15 May 2024.

Popular in

June

Cheapest in

January

Round-trip from

£442

One-way from

£72
High demand for flights, 19% 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 36% 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 £222, or £261 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 £84.

When is the cheapest time to fly from Boston to Chicago (BOS - 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 25% versus a flight in the morning.

Cheap Spirit Airlines flights from Boston to Chicago

Explore cheap flight options specifically provided by Spirit 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 852,833 searches. Data last updated 15 May 2024.
Take a look at some of the lowest-priced Spirit Airlines flights heading from Boston to Chicago. Make sure to double check the flight details before booking.
Wed 12/613:53BOS - ORD
1 stop10h 52mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£52
Wed 12/606:30BOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£60
Fri 7/612:07BOS - ORD
1 stop7h 58mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£66
Wed 12/613:53BOS - ORD
1 stop10h 52mSpirit Airlines
Tue 18/605:39ORD - BOS
1 stop10h 29mSpirit Airlines
Deal found 13/5£68
Fri 7/606:30BOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£75
Fri 7/612:07BOS - ORD
1 stop12h 14mSpirit Airlines
Tue 18/605:39ORD - BOS
1 stop10h 29mSpirit Airlines
Deal found 13/5£83
Wed 12/620:00BOS - ORD
3 stops17h 00mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£98
Fri 7/618:39BOS - ORD
3 stops22h 42mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£120
Fri 7/618:39BOS - ORD
3 stops22h 42mSpirit Airlines
Tue 18/605:39ORD - BOS
1 stop10h 29mSpirit Airlines
Deal found 13/5£138

Cheap Southwest flights from Boston to Chicago

Explore cheap flight options specifically provided by Southwest 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 852,833 searches. Data last updated 15 May 2024.
Have a look at some of the cheapest available Southwest flights departing from Boston and landing in Chicago. Check back soon if you're not seeing flights that suit your needs.
Wed 29/509:25BOS - ORD
1 stop5h 50mSouthwest
Fri 31/507:00ORD - BOS
1 stop9h 00mSouthwest
Deal found 14/5£209
Wed 29/507:50BOS - ORD
2 stops14h 40mSouthwest
Fri 31/507:00ORD - BOS
1 stop9h 00mSouthwest
Deal found 14/5£269
Mon 20/506:05BOS - ORD
1 stop4h 55mSouthwest
Wed 22/509:10ORD - BOS
2 stops9h 30mSouthwest
Deal found 14/5£321
Mon 20/506:05BOS - ORD
1 stop4h 55mSouthwest
Wed 22/509:10ORD - BOS
2 stops9h 30mSouthwest
Deal found 14/5£341
Mon 20/506:05BOS - ORD
1 stop4h 55mSouthwest
Wed 22/505:45ORD - BOS
3 stops16h 10mSouthwest
Deal found 14/5£426

Cheap Boston to Chicago flights in May & June 2024

Find cheap flight options from Boston to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 852,833 searches. Prices were last updated on 15 May 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.
Wed 12/613:53BOS - ORD
1 stop10h 52mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£52
Wed 12/606:30BOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£60
Fri 7/612:07BOS - ORD
1 stop7h 58mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£66
Wed 12/613:53BOS - ORD
1 stop10h 52mSpirit Airlines
Tue 18/605:39ORD - BOS
1 stop10h 29mSpirit Airlines
Deal found 13/5£68
Fri 7/606:30BOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£75
Fri 7/612:07BOS - ORD
1 stop12h 14mSpirit Airlines
Tue 18/605:39ORD - BOS
1 stop10h 29mSpirit Airlines
Deal found 13/5£83
Wed 12/620:00BOS - ORD
3 stops17h 00mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£98
Wed 5/606:25BOS - ORD
Nonstop2h 55mDelta
Tue 11/606:30ORD - BOS
Nonstop2h 28mDelta
Deal found 14/5£109
Wed 12/620:00BOS - ORD
3 stops17h 00mSpirit Airlines
Tue 18/609:19ORD - BOS
1 stop11h 43mSpirit Airlines
Deal found 13/5£116

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 852,833 searches. Data last updated 15 May 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 1/706:00BOS - ORD
Nonstop2h 54mJetBlue
Fri 5/710:35ORD - BOS
1 stop8h 32mJetBlue
Deal found 14/5£116
Wed 5/606:25BOS - ORD
Nonstop2h 55mDelta
Sat 8/617:52ORD - BOS
Nonstop2h 40mDelta
Deal found 14/5£117
Fri 7/618:39BOS - ORD
3 stops22h 42mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£120
Mon 16/910:59BOS - ORD
1 stop7h 11mJetBlue
Thu 26/909:05ORD - BOS
1 stop5h 03mJetBlue
Deal found 14/5£124
Tue 4/606:25BOS - ORD
Nonstop2h 55mDelta
Sat 15/617:52ORD - BOS
Nonstop2h 40mDelta
Deal found 14/5£125
Tue 4/606:25BOS - ORD
Nonstop2h 55mDelta
Sat 8/617:52ORD - BOS
Nonstop2h 40mDelta
Deal found 14/5£130
Wed 5/606:25BOS - ORD
Nonstop2h 55mDelta
Sun 9/606:30ORD - BOS
Nonstop2h 28mDelta
Deal found 14/5£133
Tue 13/806:00BOS - ORD
Nonstop2h 54mJetBlue
Fri 16/817:15ORD - BOS
1 stop6h 02mJetBlue
Deal found 14/5£137
Wed 29/506:25BOS - ORD
Nonstop2h 55mDelta
Sat 8/617:52ORD - BOS
Nonstop2h 40mDelta
Deal found 14/5£138

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 852,833 searches. Data last updated 15 May 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.
Wed 12/606:30BOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£60
Fri 7/606:30BOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 18/621:10ORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 13/5£75
Wed 5/606:25BOS - ORD
Nonstop2h 55mDelta
Tue 11/606:30ORD - BOS
Nonstop2h 28mDelta
Deal found 14/5£109
Wed 5/606:25BOS - ORD
Nonstop2h 55mDelta
Sat 8/617:52ORD - BOS
Nonstop2h 40mDelta
Deal found 14/5£117
Tue 4/606:25BOS - ORD
Nonstop2h 55mDelta
Sat 15/617:52ORD - BOS
Nonstop2h 40mDelta
Deal found 14/5£125
Tue 4/606:25BOS - ORD
Nonstop2h 55mDelta
Sat 8/617:52ORD - BOS
Nonstop2h 40mDelta
Deal found 14/5£130
Wed 5/606:10BOS - ORD
Nonstop2h 54mJetBlue
Fri 7/619:15ORD - BOS
Nonstop2h 26mJetBlue
Deal found 13/5£133
Wed 29/506:25BOS - ORD
Nonstop2h 55mDelta
Sat 8/617:52ORD - BOS
Nonstop2h 40mDelta
Deal found 14/5£138
Wed 5/606:25BOS - ORD
Nonstop2h 55mDelta
Sun 9/606:30ORD - BOS
Nonstop2h 28mDelta
Deal found 14/5£142

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 852,833 searches. Data last updated 15 May 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 23/506:25BOS - ORD
Nonstop2h 55mDelta
Fri 31/520:10ORD - BOS
Nonstop2h 36mDelta
Deal found 15/5£133
Sat 25/516:25BOS - ORD
Nonstop2h 55mJetBlue
Wed 29/508:40ORD - BOS
Nonstop2h 29mJetBlue
Deal found 13/5£150
Wed 22/506:10BOS - ORD
Nonstop2h 54mJetBlue
Wed 29/519:15ORD - BOS
Nonstop2h 26mJetBlue
Deal found 14/5£154
Wed 22/506:10BOS - ORD
Nonstop2h 54mJetBlue
Sat 25/519:15ORD - BOS
Nonstop2h 26mJetBlue
Deal found 14/5£157
Sat 25/516:25BOS - ORD
Nonstop2h 52mDelta
Thu 30/520:10ORD - BOS
Nonstop2h 36mDelta
Deal found 14/5£161
Sat 25/516:25BOS - ORD
Nonstop2h 55mJetBlue
Wed 29/508:40ORD - BOS
Nonstop2h 29mJetBlue
Deal found 14/5£170
Sat 25/516:25BOS - ORD
Nonstop2h 55mJetBlue
Sat 1/619:15ORD - BOS
Nonstop2h 26mJetBlue
Deal found 14/5£173
Thu 23/506:25BOS - ORD
Nonstop2h 55mDelta
Tue 28/520:10ORD - BOS
Nonstop2h 36mDelta
Deal found 14/5£174
Sat 25/518:40BOS - ORD
1 stop6h 18mDelta
Thu 30/506:13ORD - BOS
Nonstop2h 27mDelta
Deal found 14/5£180

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 852,833 searches. Data last updated 15 May 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.
Wed 12/613:53BOS - ORD
1 stop10h 52mSpirit Airlines
Deal found 14/5£27
Wed 12/606:30BOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 14/5£35
Tue 27/806:10BOS - ORD
1 stop11h 30mSpirit Airlines
Deal found 14/5£38
Tue 16/714:23BOS - ORD
1 stop9h 33mSpirit Airlines
Deal found 14/5£41
Fri 14/613:53BOS - ORD
1 stop10h 28mSpirit Airlines
Deal found 14/5£41
Tue 4/606:10BOS - ORD
Nonstop2h 54mJetBlue
Deal found 14/5£55
Tue 16/705:15BOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 14/5£56
Tue 13/811:44BOS - ORD
1 stop5h 46mJetBlue
Deal found 14/5£62
Wed 12/617:39BOS - ORD
2 stops19h 21mSpirit Airlines
Deal found 14/5£68

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 852,833 searches. Data last updated 15 May 2024.

Fly from

Any airport

Fly to

Any airport

Budget

£52 - £209

Route

Depart

Return

Price

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/6

1 stop10h 52m

Chicago O'Hare Intl

Tue 18/6

Nonstop2h 28m

£52

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/6

Nonstop2h 54m

Chicago O'Hare Intl

Tue 18/6

Nonstop2h 28m

£60

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/6

1 stop7h 58m

Chicago O'Hare Intl

Tue 18/6

Nonstop2h 28m

£66

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/6

1 stop10h 52m

Chicago O'Hare Intl

Tue 18/6

1 stop10h 29m

£68

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/6

Nonstop2h 54m

Chicago O'Hare Intl

Tue 18/6

Nonstop2h 28m

£75

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/6

Nonstop2h 55m

Chicago O'Hare Intl

Tue 11/6

Nonstop2h 28m

£109

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Mon 1/7

Nonstop2h 54m

Chicago O'Hare Intl

Fri 5/7

1 stop8h 32m

£116

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/6

1 stop8h 54m

Chicago O'Hare Intl

Mon 17/6

1 stop13h 17m

£194

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 29/5

1 stop5h 50m

Chicago O'Hare Intl

Fri 31/5

1 stop9h 00m

£209

Flights are sorted by cheapest first

Deals found on 13/5

When is the best time to 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 10 May 2024.
The best time to book flights from Boston to Chicago is 51 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

When is the cheapest time 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 12 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. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Chicago by month

Plan your trip from Boston to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Boston to Chicago is currently £47 while a return flight costs £105. Price data was last updated on 12 May 2024.

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 £775). 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

£478

February

£493

March

£484

April

£495

May

£520

June

£599

July

£617

August

£568

September

£532

October

£515

November

£495

December

£500

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 15 May 2024.
Read reviews from past customers who have flown Spirit Airlines, Southwest 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
6,040 reviews
Check prices

Comfort

8.1

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

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
6,040 reviews
Southwest
8.2
Very Good
6,040 reviews
Check prices

Comfort

8.1

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

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
9,152 reviews
Southwest
8.2
Very Good
6,040 reviews
Check prices

Comfort

8.1

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

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
10,691 reviews
Southwest
8.2
Very Good
6,040 reviews
Check prices

Comfort

8.1

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

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
4,483 reviews
Southwest
8.2
Very Good
6,040 reviews
Check prices

Comfort

8.1

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

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
10,959 reviews
Southwest
8.2
Very Good
6,040 reviews
Check prices

Comfort

8.1

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

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 £100 on Cheapflights?

    Yes, there are multiple flights from Boston to Chicago for under £100. The cheapest flight booked recently is on Spirit Airlines for just £52, but on average you can expect to pay £108.

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

    Cheapflights has at least 20 direct flights from Boston to Chicago under £100. A good price for a nonstop flight from Boston to Chicago is less than £141.

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

    There are currently 20+ 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, Wednesday, Thursday, Friday, Saturday.

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

    25 flight departures from Boston to Chicago per day on average.
    Early Morning (Midnight to 6am) - 32% of flight departures
    Morning (6am - Midday) - 20% of flight departures
    Afternoon (Midday - 6pm) - 32% of flight departures
    Evening (6pm - Midnight) - 16% of flight departures

  • How long is the flight from Boston to Chicago?

    A quick flight from Boston to Chicago can take about 2h 54m. Spirit Airlines provides one of the quickest options available for as low as £52. Airlines will cover a distance of 869 mi. This flight may include one or multiple stops.

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

    Currently priced at £52, Spirit Airlines will fly you from Boston to Chicago and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and JetBlue - these airlines can fly you to your destination from £109 and £116, respectively. These flights start at 76% 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 Spirit Airlines, with whom users have recently found tickets for as low as £27. However, be on the lookout for offers from JetBlue 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 LATAM Airlines (97%), ANA (97%) or Scandinavian 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 £74. On average you can expect to pay £148. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £194.

  • 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 14/5.

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

Boston to O'Hare Intl flights
Edinburgh to Dubai flights
London to Oslo flights
London Heathrow Airport to Kathmandu flights
London to Nairobi flights
London to Barcelona flights
London to Bruges flights
London to Liverpool flights
London to Guatemala City flights
London to Halkidiki flights
London to Perth flights
London to Goa flights
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.
First Class
Business Class
Prem Econ Class
Economy class

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 15 May 2024.
13%of flight departuresEarly morningMidnight to 6 am
39%of flight departuresMorning6 am to noon
42%of flight departuresAfternoonNoon to 6 pm
6%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 15 May 2024.
Monday66daily flights
Tuesday46daily flights
Wednesday52daily flights
Thursday56daily flights
Friday61daily flights
Saturday31daily flights
Sunday51daily flights

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to La Paz El Alto Intl
Flights to Lhasa
Flights to Abbotsford
Flights to Parikia Paros
Flights to Cagayan de Oro Laguindingan
Flights to Comiso
Flights to Monterey Regional
Flights to Antakya Hatay
Flights to Samarkand
Flights to Houmt Souk Melita
Flights to Yanbian Yanji Chaoyangchuan
Flights to Daraga Bicol Intl
Flights to Port Vila Bauerfield
Flights to Edremit/Korfez
Flights to Guilin
Flights to Erie
Flights to Mont Lubin Rodrigues Is
Flights to Şırnak Sirnak Serafettin Elci
Flights to Elazig
Flights to Reggio Calabria Tito Menniti
Flights to Malatya Erhac
Flights to Leh
Flights to Tulum Intl
Flights to Praya Lombok Intl

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 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.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines