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$135+ Cheap flights from Billings (BIL) to Chicago (CHI)

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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — CHI
août 23 — août 301
sam. 8/23
sam. 8/30
1 adult, Economy
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Cheap flight deals from Billings to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Billings (BIL) 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 août 18, 2025.

Round-trip from

$229
(American Airlines)

One-way from

$135
(Kiwi.com)

Popular in

November

Cheapest in

October

Average price

$294

Good round-trip deal

$330 or less

Good one-way deal

$212 or less
From Billings Logan Intl to Chicago (CHI)
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One-way flight from Billings Logan Intl to Chicago (CHI)
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Highest demand for flights based on searches. 22% potential increase in price ($120 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Billings Logan Intl to Chicago (CHI).
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Price to beat on a one-way flight from Billings Logan Intl to Chicago (CHI).
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Find flight deals from Billings to Chicago

Cheapest flights from Billings to Chicago
Explore the most affordable flight options available from Billings to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on août 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/212:19 pmBIL - ORD
Nonstop2h 54mAmerican Airlines
mar. 10/79:40 amORD - BIL
Nonstop3h 10mAmerican Airlines
Deal found 8/15$229
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/46:00 amBIL - ORD
Nonstop2h 53mAmerican Airlines
dim. 10/129:40 amORD - BIL
Nonstop3h 10mAmerican Airlines
Deal found 8/16$244
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 9/276:25 amBIL - MDW
1 stop5h 38mDelta
lun. 9/297:15 pmMDW - BIL
1 stop4h 55mDelta
Deal found 8/18$249
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 9/175:25 amBIL - ORD
1 stop5h 28mDelta
sam. 9/206:20 pmORD - BIL
1 stop5h 44mDelta
Deal found 8/16$249
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 9/65:57 pmBIL - ORD
1 stop5h 02mUnited Airlines
lun. 9/228:55 amORD - BIL
Nonstop3h 21mUnited Airlines
Deal found 8/17$254
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/305:49 amBIL - ORD
Nonstop2h 52mAmerican Airlines
mar. 9/28:46 pmORD - BIL
Nonstop3h 14mAmerican Airlines
Deal found 8/16$259
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/46:00 amBIL - ORD
Nonstop2h 53mAmerican Airlines
lun. 9/88:39 pmORD - BIL
Nonstop3h 00mAmerican Airlines
Deal found 8/18$260
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 9/66:25 amBIL - MDW
2 stops8h 03mDelta
lun. 9/227:15 pmMDW - BIL
1 stop4h 55mDelta
Deal found 8/17$269
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 9/66:25 amBIL - ORD
2 stops9h 13mDelta
lun. 9/225:15 pmORD - BIL
1 stop6h 55mDelta
Deal found 8/17$269
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 9/199:58 amBIL - ORD
1 stop10h 01mMultiple Airlines
dim. 9/211:03 pmORD - BIL
1 stop30h 52mMultiple Airlines
Deal found 8/16$271
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 9/171:59 pmBIL - ORD
1 stop9h 00mAmerican Airlines
sam. 9/208:39 pmORD - BIL
Nonstop3h 00mAmerican Airlines
Deal found 8/17$285
This American Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 9/1412:19 pmBIL - ORD
Nonstop2h 54mAmerican Airlines
dim. 9/216:00 amORD - BIL
1 stop8h 29mAmerican Airlines
Deal found 8/15$299

Cheapflights Fare Finder

 
Customize your flight search to find flights from Billings 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 2,558,603 searches. Data last updated août 18, 2025.
Use the filters below to find and compare flights from Billings to Chicago that are best for you.

Fly from

Billings

Fly to

Chicago

Route

Depart

Return

Price

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

jeu. 10/2

12:19 pm-4:13 pm

Nonstop2h 54m

Chicago O'Hare Intl

mar. 10/7

9:40 am-11:50 am

Nonstop3h 10m

$229

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

sam. 9/6

6:00 am-9:53 am

Nonstop2h 53m

Chicago O'Hare Intl

sam. 9/13

8:39 pm-10:39 pm

Nonstop3h 00m

$229

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

sam. 10/4

6:00 am-9:53 am

Nonstop2h 53m

Chicago O'Hare Intl

dim. 10/12

9:40 am-11:50 am

Nonstop3h 10m

$244

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

sam. 9/27

6:25 am-1:03 pm

1 stop5h 38m

Chicago Midway

lun. 9/29

7:15 pm-11:10 pm

1 stop4h 55m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

mar. 11/18

11:38 am-5:57 pm

1 stop5h 19m

Chicago O'Hare Intl

ven. 12/5

5:20 pm-10:44 pm

1 stop6h 24m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

sam. 11/15

6:25 am-11:31 am

1 stop4h 06m

Chicago O'Hare Intl

ven. 12/5

5:20 pm-10:44 pm

1 stop6h 24m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

mer. 9/17

5:25 am-11:53 am

1 stop5h 28m

Chicago O'Hare Intl

sam. 9/20

6:20 pm-11:04 pm

1 stop5h 44m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

jeu. 11/20

5:45 am-12:24 pm

1 stop5h 39m

Chicago O'Hare Intl

ven. 12/5

5:20 pm-10:44 pm

1 stop6h 24m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

mer. 11/19

5:45 am-12:24 pm

1 stop5h 39m

Chicago O'Hare Intl

ven. 12/5

5:20 pm-10:44 pm

1 stop6h 24m

$249

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

sam. 9/6

6:25 am-3:28 pm

2 stops8h 03m

Chicago Midway

lun. 9/22

7:15 pm-11:10 pm

1 stop4h 55m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 26 results
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Best time to book a flight from Billings to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Billings with our price prediction graph.
Estimated round-trip 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.

Cheapflights Insights

Everything you need to know about your flight from Billings to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Billings to Chicago (average of $245). Flying from Billings to Chicago in March is currently the most expensive (average of $321). 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.

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

Find hourly flight availability from Billings 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 août 18, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 17% on flights from Billings to Chicago by exploring options for tickets at noon.

Weekly flight availability from Billings to Chicago

Explore weekly flight availability from Billings 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 août 18, 2025.

The most flights from BIL to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Billings to Chicago?

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 août 18, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Billings to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,925 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Billings 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 Billings to Chicago?

    If you book a flight to Chicago from Billings, you will be flying from Billings Logan Intl, which is the city’s only airport. Billings Logan Intl (BIL) is located 2.7 mi from the center of Billings. There are 3 flights from Billings Logan Intl to Chicago per day from 3 different airlines.

  • How long is the flight from Billings to Chicago?

    For as low as $229, American Airlines can have you in Chicago from Billings in 2h 54m. Billings and Chicago are separated by a distance of 1057 mi. This flight may include one or multiple stops.

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

    According to our current data, American Airlines ($225), United Airlines ($239), and Delta ($314) offers the cheapest pricing from Billings to Chicago. Users have found that American Airlines is 45% cheaper than the other options available to this destination.

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

    The top 3 most reliable airlines when flying from Billings to Chicago are SkyWest Airlines (80%), United Airlines (80%) and American Airlines (75%).

  • What are the cheapest flights from Billings to Chicago?

    Looking for the cheapest flight from Billings to Chicago? While on average our users pay $334, our data indicates the cheapest price to be $167. The most popular route (Billings Logan Intl - Chicago O'Hare Intl), is priced around $249.

  • Can I find deals for flights from Billings to Chicago that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Billings 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.

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

    Currently, August is the cheapest month in which you can book a flight from Billings to Chicago (average of $245). Flying from Billings to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Billings to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Billings to Chicago

Discover the top 3 airlines that operate flights from Billings 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 2,558,603 searches. Data last updated août 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$390FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$542FlexibilityNo cancel feeOn-time69%
DeltaCheapest$314Average$380FlexibilityNo cancel feeOn-timeN/A

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