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$133+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — CHI
Jan 5 — Jan 121
Mon 1/5
Mon 1/12
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 6, 2025.

This United Airlines deal was found by Cheapflights users on 12/4. 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.
Tue 12/167:00 amBIL - ORD
1 stop6h 55mUnited Airlines
Fri 1/302:36 pmORD - BIL
1 stop7h 47mUnited Airlines
Deal found 12/4$324
This United Airlines deal was found by Cheapflights users on 12/4. 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.
Fri 12/192:40 pmBIL - ORD
1 stop7h 20mUnited Airlines
Tue 12/238:20 pmORD - BIL
2 stops26h 04mUnited Airlines
Deal found 12/4$488
This Delta deal was found by Cheapflights users on 12/4. 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.
Thu 12/186:25 amBIL - MDW
1 stop5h 45mDelta
Sat 12/205:59 pmMDW - BIL
1 stop6h 20mDelta
Deal found 12/4$523
This Delta deal was found by Cheapflights users on 12/3. 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.
Sun 12/216:25 amBIL - ORD
1 stop4h 25mDelta
Mon 12/296:30 pmORD - BIL
1 stop5h 49mDelta
Deal found 12/3$523
This Delta deal was found by Cheapflights users on 12/4. 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 12/56:25 amBIL - ORD
1 stop4h 15mDelta
Sun 12/75:42 pmORD - BIL
1 stop7h 06mDelta
Deal found 12/4$580
This Kiwi.com deal was found by Cheapflights users on 12/4. 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.
Thu 12/189:25 amBIL - ORD
1 stop25h 57mMultiple Airlines
Sat 12/209:55 pmORD - BIL
1 stop11h 40mMultiple Airlines
Deal found 12/4$583
This American Airlines deal was found by Cheapflights users on 12/4. 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 12/81:58 pmBIL - ORD
1 stop6h 26mAmerican Airlines
Wed 12/105:18 amORD - BIL
1 stop9h 10mAmerican Airlines
Deal found 12/4$586
This United Airlines deal was found by Cheapflights users on 12/5. 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.
Fri 12/55:54 pmBIL - ORD
1 stop5h 05mUnited Airlines
Sun 12/74:18 pmORD - BIL
1 stop6h 03mUnited Airlines
Deal found 12/5$589
This Delta deal was found by Cheapflights users on 12/6. 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.
Sun 12/215:14 amBIL - MDW
2 stops10h 06mDelta
Thu 12/255:59 pmMDW - BIL
1 stop6h 20mDelta
Deal found 12/6$838
This Delta deal was found by Cheapflights users on 12/4. 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 12/196:25 amBIL - MDW
1 stop5h 45mDelta
Tue 12/235:59 pmMDW - BIL
1 stop6h 20mDelta
Deal found 12/4$939

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 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Delta)

One-way from

$133
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$358

Good round-trip deal

$1,152 or less

Good one-way deal

$345 or less
Provider with most accurate pricing for Billings Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Billings Logan Intl-Chicago (CHI) flights.
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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. 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
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Price to beat on a round-trip flight from Billings Logan Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Billings Logan Intl to Chicago (CHI).
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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 6, 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

Thu 1/8

6:22 am-1:09 pm

1 stop5h 47m

Chicago Midway

Sun 1/11

1:49 pm-7:25 pm

1 stop6h 36m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Thu 1/22

6:10 am-11:47 am

1 stop4h 37m

Chicago O'Hare Intl

Mon 1/26

12:30 pm-7:24 pm

1 stop7h 54m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Fri 1/23

6:10 am-11:47 am

1 stop4h 37m

Chicago O'Hare Intl

Mon 1/26

12:30 pm-7:24 pm

1 stop7h 54m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Sun 1/18

6:22 am-11:47 am

1 stop4h 25m

Chicago O'Hare Intl

Sun 1/25

12:30 pm-7:24 pm

1 stop7h 54m

$249

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

Sat 2/14

2:04 pm-11:56 pm

1 stop8h 52m

Chicago O'Hare Intl

Wed 2/18

3:54 pm-11:38 pm

1 stop8h 44m

$303

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Fri 1/23

3:35 pm-11:50 pm

2 stops31h 15m

Chicago O'Hare Intl

Mon 1/26

2:06 pm-2:55 pm

2 stops25h 49m

$303

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Sat 5/9

5:45 am-12:21 pm

1 stop5h 36m

Chicago O'Hare Intl

Wed 5/13

5:20 pm-10:37 pm

1 stop6h 17m

$304

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Thu 1/8

5:15 am-12:41 pm

1 stop6h 26m

Chicago O'Hare Intl

Sun 1/11

12:30 pm-7:25 pm

1 stop7h 55m

$304

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Mon 2/2

3:35 pm-5:10 pm

2 stops24h 35m

Chicago O'Hare Intl

Sat 2/7

8:00 am-2:55 pm

1 stop7h 55m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 22 results
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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 6, 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
8,009 reviews

Entertainment

7.9

Overall

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Comfort

7.9

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
8,009 reviews
Delta
7.9
Good
8,009 reviews

Entertainment

7.9

Overall

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Comfort

7.9

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
9,065 reviews
Delta
7.9
Good
8,009 reviews

Entertainment

7.9

Overall

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Comfort

7.9

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
11,043 reviews
Delta
7.9
Good
8,009 reviews

Entertainment

7.9

Overall

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Comfort

7.9

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 47m. Billings and Chicago are separated by a distance of 1070 mi.

  • 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 $892, our data indicates the cheapest price to be $345. The most popular route (Billings Logan Intl - Chicago O'Hare Intl), is priced around $239.

  • 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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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 December 6, 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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