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$106+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — CHI
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
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 February 3, 2026.

This Delta deal was found by Cheapflights users on 2/3. 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.
Sat 4/256:24 am
BIL
-
MDW
1 stop6h 08m
Delta
Mon 4/272:12 pm
MDW
-
BIL
1 stop6h 54m
Delta
Deal found 2/3$249
This Delta deal was found by Cheapflights users on 2/3. 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.
Sat 5/95:35 am
BIL
-
ORD
1 stop5h 17m
Delta
Wed 5/135:43 pm
ORD
-
BIL
1 stop6h 20m
Delta
Deal found 2/3$249
This American Airlines deal was found by Cheapflights users on 2/2. 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 8/2712:28 pm
BIL
-
ORD
Nonstop2h 51m
American Airlines
Mon 8/318:46 pm
ORD
-
BIL
Nonstop3h 13m
American Airlines
Deal found 2/2$250
This Delta deal was found by Cheapflights users on 2/3. 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.
Sat 4/255:20 am
BIL
-
MDW
2 stops7h 12m
Delta
Tue 4/282:12 pm
MDW
-
BIL
1 stop6h 54m
Delta
Deal found 2/3$254
This United Airlines deal was found by Cheapflights users on 2/1. 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 4/102:35 pm
BIL
-
ORD
1 stop7h 19m
United Airlines
Mon 4/132:35 pm
ORD
-
BIL
1 stop7h 22m
United Airlines
Deal found 2/1$268
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Thu 2/195:53 pm
BIL
-
ORD
1 stop5h 06m
United Airlines
Tue 2/247:10 am
ORD
-
BIL
1 stop7h 13m
United Airlines
Deal found 2/2$274
This United Airlines deal was found by Cheapflights users on 2/1. 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 7/102:30 pm
BIL
-
ORD
1 stop7h 49m
United Airlines
Tue 7/145:00 am
ORD
-
BIL
1 stop5h 39m
United Airlines
Deal found 2/1$288
This Delta deal was found by Cheapflights users on 2/3. 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.
Sat 5/96:25 am
BIL
-
MDW
1 stop5h 54m
Delta
Wed 5/137:00 pm
MDW
-
BIL
1 stop5h 03m
Delta
Deal found 2/3$304
This Delta deal was found by Cheapflights users on 2/1. 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 2/246:20 am
BIL
-
MDW
1 stop5h 45m
Delta
Sun 3/11:28 pm
MDW
-
BIL
2 stops7h 11m
Delta
Deal found 2/1$309
This Delta deal was found by Cheapflights users on 2/1. 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 2/245:10 am
BIL
-
ORD
1 stop6h 09m
Delta
Sun 3/110:35 am
ORD
-
BIL
2 stops10h 04m
Delta
Deal found 2/1$309
This United Airlines deal was found by Cheapflights users on 2/1. 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 2/242:35 pm
BIL
-
ORD
1 stop7h 17m
United Airlines
Sun 3/17:10 am
ORD
-
BIL
1 stop7h 13m
United Airlines
Deal found 2/1$324
This Delta deal was found by Cheapflights users on 2/1. 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 8/275:45 am
BIL
-
ORD
1 stop5h 36m
Delta
Mon 8/315:20 pm
ORD
-
BIL
1 stop6h 17m
Delta
Deal found 2/1$325

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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(Delta)

One-way from

$106
(Delta)

Popular in

November

Cheapest in

January

Average price

$423

Good round-trip deal

$501 or less

Good one-way deal

$238 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. 2% potential increase in price ($9 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 February 2026
Search Deals
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).
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 February 3, 2026.
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

Tue 5/5

6:24 am-1:32 pm

1 stop6h 08m

Chicago Midway

Tue 5/12

7:00 pm-11:03 pm

1 stop5h 03m

$249

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sat 4/25

5:20 am-1:32 pm

2 stops7h 12m

Chicago Midway

Tue 4/28

2:12 pm-8:06 pm

1 stop6h 54m

$254

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Fri 4/10

2:35 pm-10:54 pm

1 stop7h 19m

Chicago O'Hare Intl

Mon 4/13

2:35 pm-8:57 pm

1 stop7h 22m

$268

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Fri 7/10

2:30 pm-11:19 pm

1 stop7h 49m

Chicago O'Hare Intl

Tue 7/14

5:00 am-9:39 am

1 stop5h 39m

$288

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sat 5/9

6:25 am-1:19 pm

1 stop5h 54m

Chicago Midway

Wed 5/13

7:00 pm-11:03 pm

1 stop5h 03m

$304

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Wed 2/18

6:20 am-5:37 pm

2 stops10h 17m

Chicago Midway

Mon 2/23

1:49 pm-7:39 pm

1 stop6h 50m

$304

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Tue 2/24

6:20 am-1:05 pm

1 stop5h 45m

Chicago Midway

Sun 3/1

1:28 pm-7:39 pm

2 stops7h 11m

$309

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Tue 2/24

5:10 am-12:19 pm

1 stop6h 09m

Chicago O'Hare Intl

Sun 3/1

10:35 am-7:39 pm

2 stops10h 04m

$309

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Sat 5/9

11:34 am-11:59 pm

2 stops11h 25m

Chicago O'Hare Intl

Wed 5/13

5:43 pm-11:03 pm

1 stop6h 20m

$309

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Tue 2/24

2:35 pm-10:52 pm

1 stop7h 17m

Chicago O'Hare Intl

Sun 3/1

7:10 am-1:23 pm

1 stop7h 13m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 29 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Billings-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

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

Currently, September is the cheapest month in which you can book a flight from Billings to Chicago (average of $217). Flying from Billings to Chicago in March is currently the most expensive (average of $353). 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.

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 February 3, 2026.
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
8,138 reviews

Crew

8.5

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.2

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
8,138 reviews
Delta
7.9
Good
8,138 reviews

Crew

8.5

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.2

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
9,236 reviews
Delta
7.9
Good
8,138 reviews

Crew

8.5

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.2

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
11,217 reviews
Delta
7.9
Good
8,138 reviews

Crew

8.5

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.2

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 6h 08m. 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 38% cheaper than the other options available to this destination.

  • What are the cheapest flights from Billings to Chicago?

    Looking for the cheapest flight from Billings to Chicago? While on average our users pay $586, our data indicates the cheapest price to be $204. 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.

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

    Currently, September is the cheapest month in which you can book a flight from Billings to Chicago (average of $217). Flying from Billings to Chicago in March is currently the most expensive (average of $353). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$371FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$406FlexibilityNo cancel feeOn-time69%
DeltaCheapest$248Average$447FlexibilityNo cancel feeOn-timeN/A

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