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Cheap flights from Boston (BOS) to Chicago (CHI) 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 5/22. 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
May 2 — May 91
From?
To?
Thu 5/2
Thu 5/9
1 adult, Economy
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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 April 27, 2024.

Popular in

June

Cheapest in

January

Round-trip from

$222

One-way from

$90
High demand for flights, 27% potential price rise
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Best time to find cheap flights, 39% potential price drop
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From Boston Logan Intl to Chicago (CHI)
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One-way flight from Boston Logan Intl to Chicago (CHI)
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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 27% 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 11% 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 3,068,117 searches. Data last updated April 27, 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.
Wed 6/56:10 amBOS - ORD
1 stop12h 30mSpirit Airlines
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Deal found 4/26$71
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Deal found 4/26$73
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/189:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/25$85
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/189:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/26$87
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Mon 6/179:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/26$92
Tue 5/710:01 amBOS - ORD
1 stop23h 44mSpirit Airlines
Tue 5/149:15 pmORD - BOS
2 stops20h 31mSpirit Airlines
Deal found 4/26$93
Thu 6/612:07 pmBOS - ORD
1 stop9h 34mSpirit Airlines
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Deal found 4/26$94
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/185:39 amORD - BOS
1 stop10h 29mSpirit Airlines
Deal found 4/26$95
Tue 5/711:49 amBOS - ORD
1 stop9h 41mSpirit Airlines
Tue 5/149:35 amORD - BOS
1 stop11h 01mSpirit Airlines
Deal found 4/26$96

  • 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 76% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $93.90 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 3,068,117 searches. Data last updated April 27, 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.
Sat 5/44:20 pmBOS - ORD
Nonstop3h 04mDelta
Sat 5/115:15 pmORD - BOS
Nonstop2h 29mDelta
Deal found 4/26$194
Tue 5/216:25 amBOS - ORD
Nonstop2h 55mDelta
Thu 5/308:10 pmORD - BOS
Nonstop2h 36mDelta
Deal found 4/26$203
Tue 5/2112:00 pmBOS - ORD
1 stop7h 25mDelta
Wed 5/296:27 amORD - BOS
Nonstop2h 27mDelta
Deal found 4/26$230
Tue 5/216:30 amBOS - ORD
Nonstop2h 55mDelta
Wed 5/226:05 amORD - BOS
Nonstop2h 29mDelta
Deal found 4/26$233
Thu 5/26:25 amBOS - ORD
Nonstop2h 57mDelta
Sat 5/412:30 pmORD - BOS
Nonstop2h 29mDelta
Deal found 4/25$244
Mon 5/61:15 pmBOS - ORD
1 stop5h 40mDelta
Sat 5/115:15 pmORD - BOS
Nonstop2h 29mDelta
Deal found 4/26$248
Fri 5/38:55 pmBOS - ORD
Nonstop3h 00mDelta
Wed 5/81:02 pmORD - BOS
Nonstop2h 38mDelta
Deal found 4/25$254
Fri 5/38:55 pmBOS - ORD
Nonstop3h 00mDelta
Tue 5/78:45 amORD - BOS
1 stop4h 34mDelta
Deal found 4/26$308
Sat 5/45:35 amBOS - MDW
1 stop4h 14mDelta
Sat 5/45:45 pmMDW - BOS
1 stop4h 39mDelta
Deal found 4/26$318

  • One of the most popular airlines traveling from Boston to Chicago is Delta. Flights from Delta traveling this route typically cost $371.43 RT. This price is typically 52% 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 11% more popular than any other airline flying that same route.

Cheap Boston to Chicago flights in April & May 2024

Find cheap flight options from Boston to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,068,117 searches. Prices were last updated on April 27, 2024.
The lowest fares we've come across on flights traveling from Boston to Chicago in April and May 2024. Check back in a little while for more flight options.
Tue 5/710:01 amBOS - ORD
1 stop23h 44mSpirit Airlines
Tue 5/149:15 pmORD - BOS
2 stops20h 31mSpirit Airlines
Deal found 4/26$93
Tue 5/711:49 amBOS - ORD
1 stop9h 41mSpirit Airlines
Wed 5/85:00 amORD - BOS
2 stops17h 26mSpirit Airlines
Deal found 4/26$94
Tue 5/711:49 amBOS - ORD
1 stop9h 41mSpirit Airlines
Tue 5/149:35 amORD - BOS
1 stop11h 01mSpirit Airlines
Deal found 4/26$96
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 4/26$97
Mon 5/138:21 amBOS - ORD
1 stop27h 26mFrontier
Thu 5/161:30 pmORD - BOS
1 stop19h 54mFrontier
Deal found 4/26$97
Sat 5/1112:41 pmBOS - MDW
1 stop11h 00mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 4/26$98
Wed 5/295:52 pmBOS - ORD
1 stop18h 16mSpirit Airlines
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 4/25$99
Tue 5/146:10 amBOS - ORD
1 stop18h 19mSpirit Airlines
Wed 5/155:00 amORD - BOS
2 stops17h 26mSpirit Airlines
Deal found 4/25$102
Tue 5/75:05 amBOS - ORD
1 stop13h 41mMultiple Airlines
Sat 5/118:25 amORD - BOS
1 stop22h 43mMultiple Airlines
Deal found 4/25$103

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 3,068,117 searches. Data last updated April 27, 2024.
The lowest fares we've come across on flights traveling from Boston to Chicago in April and May 2024. Check back in a little while for more flight options.
Wed 6/56:10 amBOS - ORD
1 stop12h 30mSpirit Airlines
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Deal found 4/26$71
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Deal found 4/26$73
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/189:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/25$85
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/189:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/26$87
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Mon 6/179:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/26$92
Tue 5/710:01 amBOS - ORD
1 stop23h 44mSpirit Airlines
Tue 5/149:15 pmORD - BOS
2 stops20h 31mSpirit Airlines
Deal found 4/26$93
Thu 6/612:07 pmBOS - ORD
1 stop9h 34mSpirit Airlines
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Deal found 4/26$94
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/185:39 amORD - BOS
1 stop10h 29mSpirit Airlines
Deal found 4/26$95
Tue 5/711:49 amBOS - ORD
1 stop9h 41mSpirit Airlines
Tue 5/149:35 amORD - BOS
1 stop11h 01mSpirit Airlines
Deal found 4/26$96

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 3,068,117 searches. Data last updated April 27, 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.
Wed 6/57:30 pmBOS - ORD
Nonstop2h 56mAmerican Airlines
Sat 6/88:36 pmORD - BOS
Nonstop2h 25mAmerican Airlines
Deal found 4/26$137
Wed 5/228:00 amBOS - ORD
Nonstop2h 52mUnited Airlines
Wed 5/299:45 pmORD - BOS
Nonstop2h 35mUnited Airlines
Deal found 4/26$139
Tue 5/286:00 amBOS - ORD
Nonstop2h 50mUnited Airlines
Thu 5/306:04 amORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 4/26$146
Tue 5/286:25 amBOS - ORD
Nonstop2h 55mDelta
Wed 5/296:27 amORD - BOS
Nonstop2h 27mDelta
Deal found 4/26$147
Wed 6/196:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Tue 6/259:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/26$153
Wed 6/196:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Mon 6/249:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 4/25$154
Fri 6/76:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Deal found 4/25$155
Wed 6/57:30 pmBOS - ORD
Nonstop2h 56mAmerican Airlines
Wed 6/121:30 pmORD - BOS
Nonstop2h 18mAmerican Airlines
Deal found 4/26$156
Thu 5/307:10 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Sat 6/18:39 pmORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 4/26$159

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 3,068,117 searches. Data last updated April 27, 2024.
Check out these flights departing soon from Boston to Chicago. Users should examine the flight details to ensure there are no surprises.
Sat 5/412:41 pmBOS - MDW
1 stop11h 00mFrontier
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/26$129
Sat 5/412:41 pmBOS - MDW
1 stop11h 00mFrontier
Sun 5/56:31 pmMDW - BOS
1 stop12h 37mFrontier
Deal found 4/26$133
Mon 5/69:08 amBOS - ORD
1 stop15h 35mFrontier
Thu 5/161:30 pmORD - BOS
1 stop19h 54mFrontier
Deal found 4/26$136
Mon 5/612:41 pmBOS - MDW
1 stop11h 49mFrontier
Sun 5/126:31 pmMDW - BOS
1 stop12h 37mFrontier
Deal found 4/26$146
Sun 5/59:08 amBOS - MDW
1 stop9h 32mFrontier
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/26$148
Sat 5/49:08 amBOS - ORD
1 stop15h 35mMultiple Airlines
Tue 5/712:10 pmORD - BOS
1 stop7h 35mMultiple Airlines
Deal found 4/26$148
Fri 5/39:08 amBOS - MDW
1 stop14h 23mFrontier
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/26$149
Mon 5/610:27 amBOS - ORD
2 stops24h 11mSpirit Airlines
Tue 5/78:59 pmORD - BOS
2 stops25h 56mSpirit Airlines
Deal found 4/26$151
Mon 5/610:27 amBOS - ORD
2 stops24h 11mSpirit Airlines
Wed 5/85:00 amORD - BOS
2 stops17h 26mSpirit Airlines
Deal found 4/26$152

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 3,068,117 searches. Data last updated April 27, 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.
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Deal found 4/26$54
Sat 5/1112:41 pmBOS - MDW
1 stop11h 00mFrontier
Deal found 4/26$55
Sat 5/1112:41 pmBOS - MDW
1 stop11h 00mFrontier
Deal found 4/26$60
Wed 5/298:19 amBOS - MDW
1 stop6h 50mFrontier
Deal found 4/26$65
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/26$66
Sat 6/112:59 pmBOS - MDW
1 stop7h 58mFrontier
Deal found 4/26$70
Sat 5/49:08 amBOS - MDW
1 stop11h 19mFrontier
Deal found 4/26$71
Wed 6/57:49 amBOS - MDW
1 stop6h 38mFrontier
Deal found 4/25$72
Mon 5/2010:04 amBOS - MDW
1 stop8h 31mFrontier
Deal found 4/26$73

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 3,068,117 searches. Data last updated April 27, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$71 - $174

Route

Depart

Return

Price

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/5

1 stop12h 30m

Chicago O'Hare Intl

Wed 6/12

Nonstop2h 29m

$71

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/11

Nonstop2h 54m

Chicago O'Hare Intl

Wed 6/12

Nonstop2h 29m

$73

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/12

Nonstop2h 54m

Chicago O'Hare Intl

Tue 6/18

Nonstop2h 28m

$85

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 5/13

1 stop11h 49m

Chicago Midway

Sat 5/18

1 stop11h 35m

$97

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Mon 5/13

1 stop27h 26m

Chicago O'Hare Intl

Thu 5/16

1 stop19h 54m

$97

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/7

1 stop13h 41m

Chicago O'Hare Intl

Sat 5/11

1 stop22h 43m

$103

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/5

Nonstop2h 56m

Chicago O'Hare Intl

Sat 6/8

Nonstop2h 25m

$137

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/28

Nonstop2h 50m

Chicago O'Hare Intl

Thu 5/30

Nonstop2h 20m

$146

Boston Logan IntlChicago O'Hare Intl

BOS - ORD

BOSORD

Boston Logan Intl

Sun 5/26

Nonstop2h 54m

Chicago O'Hare Intl

Thu 5/30

Nonstop2h 26m

$174

Flights are sorted by cheapest first

Deals found on 4/26

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 April 21, 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 $65 while a round-trip flight costs $109. Price data was last updated on April 21, 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 $356). 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

$273

May

$282

June

$356

July

$336

August

$276

September

$258

October

$248

November

$270

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 April 27, 2024.
See what other customers who have flown with Spirit Airlines, Delta and American 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
6,165 reviews
Check prices

Food

7.4

Entertainment

7.8

Crew

8.7

Overall

8.2

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

Southwest
8.2
Very good
6,165 reviews
Southwest
8.2
Very good
6,165 reviews
Check prices

Food

7.4

Entertainment

7.8

Crew

8.7

Overall

8.2

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

Alaska Airlines
8.1
Very good
9,117 reviews
Southwest
8.2
Very good
6,165 reviews
Check prices

Food

7.4

Entertainment

7.8

Crew

8.7

Overall

8.2

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

Delta
8.1
Very good
10,951 reviews
Southwest
8.2
Very good
6,165 reviews
Check prices

Food

7.4

Entertainment

7.8

Crew

8.7

Overall

8.2

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

JetBlue
7.6
Good
4,593 reviews
Southwest
8.2
Very good
6,165 reviews
Check prices

Food

7.4

Entertainment

7.8

Crew

8.7

Overall

8.2

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

Porter Airlines
7.4
Good
438 reviews
Southwest
8.2
Very good
6,165 reviews
Check prices

Food

7.4

Entertainment

7.8

Crew

8.7

Overall

8.2

Boarding

8.3

Comfort

8.1

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

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 Spirit Airlines for just $71, but on average you can expect to pay $95.

  • 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 $160.

  • 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: Sunday, Monday, Tuesday, Wednesday, Thursday, Saturday.

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

    50 flight departures from Boston to Chicago per day on average.
    Early Morning (Midnight to 6am) - 14% of flight departures
    Morning (6am - Noon) - 42% of flight departures
    Afternoon (Noon - 6pm) - 34% of flight departures
    Evening (6pm - Midnight) - 10% of flight departures

  • How long is the flight from Boston to Chicago?

    For as low as $71, Spirit Airlines 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $71 on this airline. An additional option worth looking into is Frontier, starting at $97. You may be able to fly from Boston to Chicago for 72% 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 $54. JetBlue flights start at $90 while deals on Spirit Airlines start at $92 one-way.

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

    Most travelers choose Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway or Boston Logan Intl - Chicago Greater Rockford when deciding on the best route from Boston to Chicago.

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

    The most popular airlines flying from Boston to Chicago are Undisclosed Carrier, American Airlines and Alaska Airlines. Something to consider prior to booking your flight.

  • 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: Scandinavian Airlines (97%), LATAM Airlines (97%), ANA (96%).

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is $89. On average you can expect to pay $684. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $73.

  • 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.

  • 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 vacation 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 4/26.

See more FAQs

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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 April 27, 2024.

United Airlines flights from Boston Logan Intl to Chicago
American Airlines flights from Boston Logan Intl to Chicago
Delta flights from Boston Logan Intl to Chicago

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 3,068,117 searches. Data last updated April 27, 2024.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$39Average$94FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
JetBlueCheapest$79Average$233FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
United AirlinesCheapest$89Average$322FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapest$94Average$371FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
FrontierCheapest$97Average$147FlexibilityNo cancel feeOn-time62%
Search Frontier flights
American AirlinesCheapest$108Average$266FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Spirit AirlinesCheapest$112Average$197FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
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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 April 27, 2024.
3%of flight departuresEarly morningMidnight to 6 am
38%of flight departuresMorning6 am to noon
55%of flight departuresAfternoonNoon to 6 pm
4%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 April 27, 2024.
Sunday51daily flights
Monday66daily flights
Tuesday46daily flights
Wednesday52daily flights
Thursday56daily flights
Friday61daily flights
Saturday31daily flights

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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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