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$118+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — CHI
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
1 adult, Economy
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Cheap 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 December 14, 2025.

This Delta deal was found by Cheapflights users on 12/11. 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.
Sat 12/136:25 amBIL - ORD
1 stop4h 18mDelta
Tue 12/165:42 pmORD - BIL
1 stop7h 06mDelta
Deal found 12/11$509
This United Airlines deal was found by Cheapflights users on 12/12. 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.
Wed 12/172:40 pmBIL - ORD
1 stop5h 28mUnited Airlines
Sat 12/202:31 pmORD - BIL
1 stop7h 53mUnited Airlines
Deal found 12/12$534
This American Airlines deal was found by Cheapflights users on 12/12. 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.
Thu 12/186:00 amBIL - ORD
1 stop8h 45mAmerican Airlines
Mon 12/221:15 pmORD - BIL
1 stop8h 59mAmerican Airlines
Deal found 12/12$550
This American Airlines deal was found by Cheapflights users on 12/12. 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.
Sat 12/131:58 pmBIL - ORD
1 stop8h 42mAmerican Airlines
Tue 12/165:18 amORD - BIL
1 stop9h 10mAmerican Airlines
Deal found 12/12$555
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Mon 12/226:50 amBIL - ORD
1 stop10h 02mAmerican Airlines
Mon 12/228:58 pmORD - BIL
1 stop17h 26mAmerican Airlines
Deal found 12/11$566
This United Airlines deal was found by Cheapflights users on 12/12. 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.
Mon 12/155:54 pmBIL - ORD
1 stop5h 05mUnited Airlines
Thu 12/187:10 amORD - BIL
1 stop7h 14mUnited Airlines
Deal found 12/12$651
This United Airlines deal was found by Cheapflights users on 12/12. 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.
Sat 12/137:00 amBIL - ORD
1 stop5h 15mUnited Airlines
Tue 12/169:25 amORD - BIL
2 stops12h 56mUnited Airlines
Deal found 12/12$681
This United Airlines deal was found by Cheapflights users on 12/13. 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.
Sun 12/282:40 pmBIL - ORD
1 stop7h 20mUnited Airlines
Thu 1/18:45 amORD - BIL
1 stop5h 39mUnited Airlines
Deal found 12/13$708
This American Airlines deal was found by Cheapflights users on 12/12. 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.
Tue 12/231:54 pmBIL - ORD
1 stop6h 25mAmerican Airlines
Tue 12/302:50 pmORD - BIL
1 stop7h 24mAmerican Airlines
Deal found 12/12$709
This Delta deal was found by Cheapflights users on 12/12. 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.
Sat 12/275:15 amBIL - MDW
2 stops11h 11mDelta
Wed 12/315:59 pmMDW - BIL
1 stop6h 20mDelta
Deal found 12/12$734
This Delta deal was found by Cheapflights users on 12/12. 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.
Tue 12/236:20 pmBIL - MDW
2 stops13h 45mDelta
Tue 12/305:59 pmMDW - BIL
1 stop6h 20mDelta
Deal found 12/12$798
This Delta deal was found by Cheapflights users on 12/14. 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.
Fri 12/265:14 amBIL - MDW
2 stops10h 06mDelta
Mon 12/295:59 pmMDW - BIL
1 stop6h 20mDelta
Deal found 12/14$1,424

Find 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 December 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Delta)

One-way from

$118
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$358

Good round-trip deal

$700 or less
Provider with most accurate pricing for Billings Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Billings Logan Intl-Chicago (CHI) flights.
Search Deals
From Billings Logan Intl to Chicago (CHI)
Search Deals
One-way flight from Billings Logan Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Billings Logan Intl to Chicago (CHI).
Search Deals

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 December 14, 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 - MDW

BILMDW

Billings Logan Intl

Wed 2/11

6:10 am-1:06 pm

1 stop5h 56m

Chicago Midway

Wed 2/18

1:49 pm-7:39 pm

1 stop6h 50m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Thu 2/12

2:35 pm-10:52 pm

1 stop7h 17m

Chicago O'Hare Intl

Wed 2/18

2:40 pm-9:22 pm

1 stop7h 42m

$249

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Fri 2/13

6:20 am-1:07 pm

1 stop5h 47m

Chicago Midway

Wed 2/18

1:49 pm-7:39 pm

1 stop6h 50m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Sat 2/14

5:10 am-12:19 pm

1 stop6h 09m

Chicago O'Hare Intl

Mon 2/16

3:59 pm-7:39 pm

1 stop4h 40m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Thu 2/12

5:10 am-12:19 pm

1 stop6h 09m

Chicago O'Hare Intl

Mon 2/16

3:59 pm-7:39 pm

1 stop4h 40m

$249

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Tue 2/10

6:10 am-5:55 pm

2 stops10h 45m

Chicago Midway

Wed 2/18

1:49 pm-7:39 pm

1 stop6h 50m

$254

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Tue 2/10

6:15 pm-9:53 am

2 stops14h 38m

Chicago Midway

Tue 2/17

1:49 pm-7:39 pm

1 stop6h 50m

$254

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Tue 2/10

6:15 pm-8:42 am

2 stops13h 27m

Chicago O'Hare Intl

Mon 2/16

3:59 pm-7:39 pm

1 stop4h 40m

$254

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Thu 3/26

6:25 am-1:23 pm

1 stop5h 58m

Chicago Midway

Mon 3/30

2:03 pm-8:20 pm

1 stop7h 17m

$270

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Mon 2/2

2:15 pm-10:09 pm

1 stop6h 54m

Chicago O'Hare Intl

Sat 2/7

6:54 am-1:36 pm

1 stop7h 42m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 29 results
1
2
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Compare providers for flights from Billings to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Billings to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Billings-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Billings-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Billings-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Billings-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Billings-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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
No data available for this route at this time. Please check back soon.

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 December 14, 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
7.9
Good
8,007 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,094 reviews
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Food

7.3

Overall

7.9

Boarding

8.1

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 0 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 $249, Delta can have you in Chicago from Billings in 5h 56m. Billings and Chicago are separated by a distance of 1070 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 ($248) offers the cheapest pricing from Billings to Chicago. Users have found that American Airlines is 37% 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 American Airlines (93%), Envoy Air (93%) and SkyWest Airlines (92%).

  • What are the cheapest flights from Billings to Chicago?

    Looking for the cheapest flight from Billings to Chicago? While on average our users pay $1,546, our data indicates the cheapest price to be $539. 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.

See more FAQs

Traveling to a place near Chicago?

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

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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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$370FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$413FlexibilityNo cancel feeOn-time69%
DeltaCheapest$248Average$447FlexibilityNo cancel feeOn-timeN/A

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