Cheap flights from Boston (BOS) to Chicago (CHI) from $49

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 4/9. 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
Mar 23 — Mar 301

The best prices from Boston Logan Intl to Chicago are usually found in January or February, booked 54 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 March 19, 2024.

Popular in

June

Cheapest in

January

Round-trip from

$223

One-way from

$73
High demand for flights, 27% potential price rise
Best time to find cheap flights, 39% potential price drop
From Boston Logan Intl to Chicago (CHI)
One-way flight from Boston Logan Intl to Chicago (CHI)

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

Travelers have found that booking a Monday departure is the best way to save up to 31% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 55 days in advance, which can save you up to 24% on flights from Boston to Chicago compared to booking the week you need them. Waiting 55 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $237. For sooner than that we have options available in the next 3 days from $310.

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

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Boston in January are about $260 on average during January, but can be found for as low as $79.

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

Unlike at noon, when flights are generally more expensive, you can save up to 14% on flights from Boston to Chicago by exploring options for tickets in the evening.

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 3,145,932 searches. Data last updated March 19, 2024.
Consider these cheap Spirit Airlines flights we've found departing from Boston to Chicago. It's recommended that users confirm their flight details before booking.
Thu 4/410:37 pmBOS - ORD
1 stop13h 36mSpirit Airlines
Tue 4/97:25 amORD - BOS
1 stop8h 20mSpirit Airlines
Deal found 3/17$113
Thu 4/410:37 pmBOS - ORD
1 stop13h 36mSpirit Airlines
Tue 4/97:25 amORD - BOS
1 stop8h 20mSpirit Airlines
Deal found 3/16$116
Wed 5/155:52 pmBOS - ORD
1 stop18h 16mSpirit Airlines
Mon 5/207:35 amORD - BOS
1 stop13h 02mSpirit Airlines
Deal found 3/16$120
Sat 5/410:56 pmBOS - ORD
1 stop12h 36mSpirit Airlines
Thu 5/97:35 amORD - BOS
1 stop13h 02mSpirit Airlines
Deal found 3/17$125
Mon 4/810:37 pmBOS - ORD
1 stop14h 51mSpirit Airlines
Tue 4/168:59 pmORD - BOS
1 stop11h 07mSpirit Airlines
Deal found 3/17$130
Thu 4/410:37 pmBOS - ORD
1 stop13h 36mSpirit Airlines
Tue 4/97:25 amORD - BOS
1 stop8h 20mSpirit Airlines
Deal found 3/18$132
Mon 4/810:37 pmBOS - ORD
1 stop14h 51mSpirit Airlines
Thu 4/117:40 amORD - BOS
2 stops15h 19mSpirit Airlines
Deal found 3/17$134
Mon 3/253:56 pmBOS - ORD
1 stop9h 21mSpirit Airlines
Sat 3/3012:51 pmORD - BOS
1 stop9h 23mSpirit Airlines
Deal found 3/16$164
Tue 3/269:58 amBOS - ORD
2 stops12h 12mSpirit Airlines
Thu 3/285:00 amORD - BOS
1 stop12h 33mSpirit Airlines
Deal found 3/17$166
  • If you’re traveling from Boston to Chicago, one of the more common airlines traveling that route is Spirit Airlines. Boston to Chicago flights are typically 118% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $96.40 RT. The cheapest Spirit Airlines flight found for this route was $39. When traveling from Boston to Chicago on Spirit Airlines, the most popular airport to depart from is Boston Logan Intl Airport and the most popular airport to arrive at is Chicago O'Hare Intl Airport. When flying from Boston to Chicago, Spirit Airlines flights are 11% more popular than any other airline flying that same route.

Cheap Delta flights from Boston to Chicago

Explore cheap flight options specifically provided by Delta 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 3,145,932 searches. Data last updated March 19, 2024.
Have a look at some of the cheapest available Delta flights departing from Boston and landing in Chicago. Check back soon if you're not seeing flights that suit your needs.
Tue 5/76:25 amBOS - ORD
Nonstop2h 54mDelta
Tue 5/148:05 pmORD - BOS
Nonstop2h 35mDelta
Deal found 3/17$127
Wed 5/86:25 amBOS - ORD
Nonstop2h 54mDelta
Thu 5/96:25 amORD - BOS
Nonstop2h 29mDelta
Deal found 3/18$153
Sat 4/278:05 amBOS - ORD
Nonstop2h 55mDelta
Tue 4/308:15 pmORD - BOS
Nonstop2h 32mDelta
Deal found 3/17$159
Fri 4/268:55 pmBOS - ORD
Nonstop2h 57mDelta
Tue 4/306:15 amORD - BOS
Nonstop2h 20mDelta
Deal found 3/18$174
Wed 3/2710:30 amBOS - ORD
Nonstop2h 58mDelta
Sun 3/317:59 pmORD - BOS
Nonstop2h 23mDelta
Deal found 3/17$188
Sat 4/278:05 amBOS - ORD
Nonstop2h 55mDelta
Thu 5/28:15 pmORD - BOS
Nonstop2h 32mDelta
Deal found 3/17$194
Fri 4/266:25 amBOS - ORD
Nonstop2h 56mDelta
Mon 4/298:15 pmORD - BOS
Nonstop2h 32mDelta
Deal found 3/18$209
Sun 3/242:00 pmBOS - ORD
Nonstop3h 03mDelta
Sun 3/317:59 pmORD - BOS
Nonstop2h 23mDelta
Deal found 3/18$223
Thu 5/236:25 amBOS - ORD
Nonstop2h 54mDelta
Wed 5/297:30 amORD - BOS
1 stop7h 48mDelta
Deal found 3/18$230
  • One of the most popular airlines traveling from Boston to Chicago is Delta. Flights from Delta traveling this route typically cost $363.21 RT. This price is typically 35% cheaper than other airlines that offer Boston to Chicago flights. When booking this route, the cheapest RT price found was $94. Boston Logan Intl Airport is the most common Boston airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Boston to Chicago, Delta flights are 10% more popular than any other airline flying that same route.

Cheap Boston to Chicago flights in March & April 2024

Find cheap flight options from Boston to Chicago specifically for the months of March and April 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,145,932 searches. Prices were last updated on March 19, 2024.
The lowest fares we've come across on flights traveling from Boston to Chicago in March and April 2024. Check back in a little while for more flight options.
Sat 4/2712:41 pmBOS - MDW
1 stop11h 00mFrontier
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 3/18$95
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Mon 4/153:44 pmMDW - BOS
1 stop15h 24mFrontier
Deal found 3/18$96
Tue 4/911:53 amBOS - MDW
1 stop6h 08mFrontier
Sat 4/138:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 3/18$97
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Thu 4/115:56 pmMDW - BOS
1 stop13h 12mFrontier
Deal found 3/16$98
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Sun 4/146:31 pmMDW - BOS
1 stop12h 37mFrontier
Deal found 3/18$107
Wed 4/2412:46 pmBOS - MDW
1 stop11h 44mFrontier
Sun 4/286:27 pmMDW - BOS
1 stop12h 41mFrontier
Deal found 3/17$108
Tue 4/911:53 amBOS - MDW
1 stop6h 08mFrontier
Tue 4/1612:53 pmMDW - BOS
1 stop17h 28mFrontier
Deal found 3/17$110
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Fri 4/123:44 pmMDW - BOS
1 stop15h 24mFrontier
Deal found 3/17$111
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Sun 4/146:31 pmMDW - BOS
1 stop12h 37mFrontier
Deal found 3/16$113

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 3,145,932 searches. Data last updated March 19, 2024.
The lowest fares we've come across on flights traveling from Boston to Chicago in March and April 2024. Check back in a little while for more flight options.
Sat 4/2712:41 pmBOS - MDW
1 stop11h 00mFrontier
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 3/18$95
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Mon 4/153:44 pmMDW - BOS
1 stop15h 24mFrontier
Deal found 3/18$96
Tue 4/911:53 amBOS - MDW
1 stop6h 08mFrontier
Sat 4/138:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 3/18$97
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Thu 4/115:56 pmMDW - BOS
1 stop13h 12mFrontier
Deal found 3/16$98
Wed 5/18:21 amBOS - ORD
1 stop27h 26mFrontier
Thu 5/25:51 pmORD - BOS
1 stop13h 17mFrontier
Deal found 3/18$100
Sat 5/412:41 pmBOS - MDW
1 stop11h 00mFrontier
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 3/17$103
Wed 5/112:46 pmBOS - MDW
1 stop11h 44mFrontier
Sun 5/56:31 pmMDW - BOS
1 stop12h 37mFrontier
Deal found 3/18$106
Wed 5/18:21 amBOS - ORD
1 stop27h 26mFrontier
Sun 5/55:51 pmORD - BOS
1 stop13h 17mFrontier
Deal found 3/18$106
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Sun 4/146:31 pmMDW - BOS
1 stop12h 37mFrontier
Deal found 3/18$107

Non-stop flights to Chicago from Boston

Discover non-stop flight options from Boston to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.
For a quicker trip, book one of these direct flights from Boston to Chicago. Search for alternative flights from Boston to Chicago by utilizing the search form above.
Tue 5/76:25 amBOS - ORD
Nonstop2h 54mDelta
Tue 5/148:05 pmORD - BOS
Nonstop2h 35mDelta
Deal found 3/17$127
Sat 5/46:00 amBOS - ORD
Nonstop2h 53mJetBlue
Wed 5/88:28 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 3/17$133
Tue 4/2310:15 amBOS - ORD
Nonstop2h 54mDelta
Tue 4/306:15 amORD - BOS
Nonstop2h 20mDelta
Deal found 3/16$139
Wed 5/298:00 amBOS - ORD
Nonstop2h 50mUnited Airlines
Wed 6/56:04 amORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 3/17$146
Tue 5/72:10 pmBOS - ORD
Nonstop2h 53mDelta
Thu 5/96:25 amORD - BOS
Nonstop2h 29mDelta
Deal found 3/18$153
Wed 6/126:00 amBOS - ORD
Nonstop2h 50mUnited Airlines
Tue 6/186:04 amORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 3/18$157
Sat 4/278:05 amBOS - ORD
Nonstop2h 55mDelta
Wed 5/18:15 pmORD - BOS
Nonstop2h 32mDelta
Deal found 3/17$159
Tue 4/98:10 amBOS - ORD
Nonstop2h 58mJetBlue
Tue 4/1610:55 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 3/17$163
Tue 4/97:00 amBOS - ORD
Nonstop3h 11mAmerican Airlines
Wed 4/101:35 pmORD - BOS
Nonstop2h 14mAmerican Airlines
Deal found 3/17$165

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 3,145,932 searches. Data last updated March 19, 2024.
Check out these flights departing soon from Boston to Chicago. Users should examine the flight details to ensure there are no surprises.
Tue 3/268:21 amBOS - MDW
1 stop9h 40mFrontier
Wed 3/278:43 pmMDW - BOS
1 stop11h 02mFrontier
Deal found 3/17$140
Tue 3/268:21 amBOS - MDW
1 stop9h 40mFrontier
Fri 3/298:43 pmMDW - BOS
1 stop11h 02mFrontier
Deal found 3/17$143
Tue 3/268:21 amBOS - MDW
1 stop9h 40mFrontier
Wed 3/273:16 pmMDW - BOS
1 stop15h 15mFrontier
Deal found 3/18$153
Wed 3/279:45 amBOS - ORD
1 stop11h 07mMultiple Airlines
Tue 4/97:25 amORD - BOS
1 stop8h 20mMultiple Airlines
Deal found 3/17$160
Mon 3/258:21 amBOS - MDW
1 stop9h 40mFrontier
Mon 4/18:43 pmMDW - BOS
1 stop11h 02mFrontier
Deal found 3/18$162
Mon 3/253:56 pmBOS - ORD
1 stop9h 21mSpirit Airlines
Sat 3/3012:51 pmORD - BOS
1 stop9h 23mSpirit Airlines
Deal found 3/16$164
Tue 3/269:58 amBOS - ORD
2 stops12h 12mSpirit Airlines
Thu 3/285:00 amORD - BOS
1 stop12h 33mSpirit Airlines
Deal found 3/17$166
Tue 3/268:21 amBOS - MDW
1 stop9h 40mFrontier
Tue 3/267:58 pmMDW - BOS
1 stop11h 47mFrontier
Deal found 3/18$169
Tue 3/263:50 pmBOS - ORD
1 stop6h 20mSpirit Airlines
Thu 3/285:00 amORD - BOS
1 stop12h 33mSpirit Airlines
Deal found 3/17$174

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 3,145,932 searches. Data last updated March 19, 2024.
If you're seeking multiple options on one-way flights from Boston to Chicago, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Boston to Chicago should utilize the search form at the the top of the page.
Tue 4/911:53 amBOS - MDW
1 stop6h 08mFrontier
Deal found 3/17$49
Tue 3/2611:53 amBOS - MDW
1 stop6h 08mFrontier
Deal found 3/17$50
Wed 4/1712:46 pmBOS - MDW
1 stop11h 37mFrontier
Deal found 3/17$55
Tue 4/3010:21 amBOS - MDW
1 stop14h 55mFrontier
Deal found 3/18$57
Wed 5/229:16 amBOS - MDW
1 stop13h 39mFrontier
Deal found 3/17$58
Wed 5/229:16 amBOS - MDW
1 stop13h 39mFrontier
Deal found 3/17$59
Sat 4/2012:41 pmBOS - MDW
1 stop11h 00mFrontier
Deal found 3/18$60
Mon 4/226:52 pmBOS - ORD
1 stop14h 36mSpirit Airlines
Deal found 3/18$65
Wed 4/38:21 amBOS - MDW
1 stop9h 40mFrontier
Deal found 3/18$69

Find flights from Boston to Chicago within your budget

Customize 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 3,145,932 searches. Data last updated March 19, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$96 - $165

Route

Depart

Return

Price

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 4/29

1 stop11h 49m

Chicago Midway

Sat 5/4

1 stop10h 51m

$96

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 4/9

1 stop9h 40m

Chicago Midway

Sat 4/13

1 stop10h 51m

$98

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/1

1 stop27h 26m

Chicago O'Hare Intl

Thu 5/2

1 stop13h 17m

$100

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/4

1 stop13h 36m

Chicago O'Hare Intl

Tue 4/9

1 stop8h 20m

$113

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Mon 5/6

1 stop27h 26m

Chicago O'Hare Intl

Thu 5/9

1 stop13h 02m

$119

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/7

Nonstop2h 54m

Chicago O'Hare Intl

Tue 5/14

Nonstop2h 35m

$127

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/4

Nonstop2h 53m

Chicago O'Hare Intl

Wed 5/8

Nonstop2h 26m

$133

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/29

Nonstop2h 50m

Chicago O'Hare Intl

Wed 6/5

Nonstop2h 20m

$146

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/9

Nonstop3h 11m

Chicago O'Hare Intl

Wed 4/10

Nonstop2h 14m

$165

Flights are sorted by cheapest first

Deals found on 3/18

When is the best time to book a flight from Boston to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Chicago. Price data was last updated on January 28, 2024.
The best time to book flights from Boston to Chicago is 54 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 round-trip from Boston to Chicago. Price data was last updated on March 10, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Boston to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon 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 $58 while a round-trip flight costs $122. Price data was last updated on March 10, 2024.

Currently, February is the cheapest month in which you can book a flight from Boston to Chicago (average of $245). Flying from Boston to Chicago in June is currently the most expensive (average of $361). 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

$248

February

$245

March

$280

April

$288

May

$292

June

$361

July

$338

August

$276

September

$258

October

$248

November

$271

December

$248

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

23 - 73.4 °F

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 March 19, 2024.
See what other customers who have flown with Spirit Airlines, Delta and United Airlines from Boston to Chicago have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
6,382 reviews

Overall

8.2

Comfort

8.1

Boarding

8.3

Crew

8.8

Entertainment

7.9

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.2
Very good
6,382 reviews
Southwest
8.2
Very good
6,382 reviews

Overall

8.2

Comfort

8.1

Boarding

8.3

Crew

8.8

Entertainment

7.9

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

8.1
Very good
9,147 reviews
Southwest
8.2
Very good
6,382 reviews

Overall

8.2

Comfort

8.1

Boarding

8.3

Crew

8.8

Entertainment

7.9

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

8.1
Very good
11,551 reviews
Southwest
8.2
Very good
6,382 reviews

Overall

8.2

Comfort

8.1

Boarding

8.3

Crew

8.8

Entertainment

7.9

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.7
Good
4,934 reviews
Southwest
8.2
Very good
6,382 reviews

Overall

8.2

Comfort

8.1

Boarding

8.3

Crew

8.8

Entertainment

7.9

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.4
Good
11,618 reviews
Southwest
8.2
Very good
6,382 reviews

Overall

8.2

Comfort

8.1

Boarding

8.3

Crew

8.8

Entertainment

7.9

Food

7.4

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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?

    Located just 2.6 mi from the city center, Boston Logan Intl is the airport most travelers will use when flying to Chicago from Boston. Booking flights from Logan Intl (BOS) to Chicago should be relatively easy as there are 51 daily outbound flights to Chicago from 8 different airlines.

  • 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 Frontier for just $96, but on average you can expect to pay $110.

  • 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 $163.

  • 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 nonstop flights available from Boston to Chicago?

    You can find nonstop flights on the following days: Monday, Saturday.

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

    6 flight departures from Boston to Chicago per day on average.
    Morning (6am - Noon) - 33% of flight departures
    Afternoon (Noon - 6pm) - 17% of flight departures
    Evening (6pm - Midnight) - 50% of flight departures

  • How long is the flight from Boston to Chicago?

    For as low as $96, Frontier can have you in Chicago from Boston in 11h 49m. 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?

    Our cheapest airline available from Boston to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $96 on this airline. An additional option worth looking into is Spirit Airlines, starting at $113. You may be able to fly from Boston to Chicago for 63% less than the average price by searching for these airlines.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $49. Spirit Airlines flights start at $65 while deals on JetBlue start at $70 one-way.

  • What are the most popular routes from Boston to Chicago?

  • What are the most popular airlines that fly from Boston to Chicago?

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Boston to Chicago on time: KLM (100%), Emirates (100%), Republic Airways (97%).

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is $83. On average you can expect to pay $700. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $112.

  • What does BOS to ORD mean?

    BOS and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. BOS to ORD refers to a flight route from Boston Logan Intl Airport to Chicago O'Hare Intl Airport. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

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.

Fly from Boston to Chicago on these airlines
Choose from the following airlines for your flight from Boston to Chicago. Flights are based on user searches made on Cheapflights and were last updated on March 19, 2024.

Top 7 airlines flying from Boston to Chicago

Discover the top 7 airlines that operate flights from Boston to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$39Average$96FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
JetBlueCheapest$79Average$242FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
United AirlinesCheapest$89Average$291FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapest$94Average$363FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
FrontierCheapest$100Average$147FlexibilityNo cancel feeOn-time62%
Search Frontier flights
American AirlinesCheapest$106Average$265FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Spirit AirlinesCheapest$132Average$219FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines 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.

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 March 19, 2024.
31%of flight departuresEarly morningMidnight to 6 am
28%of flight departuresMorning6 am to noon
36%of flight departuresAfternoonNoon to 6 pm
5%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
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 March 19, 2024.
Sunday51daily flights
Monday66daily flights
Tuesday46daily flights
Wednesday52daily flights
Thursday56daily flights
Friday61daily flights
Saturday31daily flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers 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?

Cheapflights makes it easy to find Boston to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

Millions of users choose and trust Cheapflights to book the best flight deals from Boston to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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

Yes, we can. To see specific flights from Boston to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes! Start tracking prices for Boston to Chicago 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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