HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$132+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — CHI
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Billings to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 11/245:21 pmBIL - ORD
1 stop25h 18mMultiple Airlines
Tue 12/24:58 pmORD - BIL
1 stop19h 19mMultiple Airlines
Deal found 10/19$228
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 11/245:21 pmBIL - ORD
1 stop25h 18mMultiple Airlines
Thu 12/49:53 pmORD - BIL
2 stops38h 49mMultiple Airlines
Deal found 10/19$242
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 11/245:21 pmBIL - ORD
1 stop25h 18mMultiple Airlines
Wed 12/34:01 pmORD - BIL
2 stops42h 11mMultiple Airlines
Deal found 10/19$248
This Delta deal was found by Cheapflights users on 10/20. 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.
Wed 11/195:18 amBIL - ORD
1 stop6h 20mDelta
Wed 11/267:40 pmORD - BIL
1 stop5h 30mDelta
Deal found 10/20$249
This Delta deal was found by Cheapflights users on 10/19. 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 11/276:25 amBIL - ORD
1 stop4h 09mDelta
Mon 12/15:42 pmORD - BIL
2 stops7h 28mDelta
Deal found 10/19$254
This Delta deal was found by Cheapflights users on 10/19. 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 11/236:25 amBIL - MDW
1 stop5h 42mDelta
Tue 12/27:02 pmMDW - BIL
1 stop5h 46mDelta
Deal found 10/19$294
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 11/245:21 pmBIL - ORD
1 stop25h 18mMultiple Airlines
Sun 11/307:57 pmORD - BIL
1 stop14h 08mMultiple Airlines
Deal found 10/19$311
This Delta deal was found by Cheapflights users on 10/19. 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 11/255:18 amBIL - ORD
2 stops10h 34mDelta
Mon 12/13:52 pmORD - BIL
2 stops9h 18mDelta
Deal found 10/19$320
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Sun 12/1410:24 pmBIL - ORD
2 stops20h 53mMultiple Airlines
Thu 12/189:33 pmORD - BIL
1 stop17h 35mMultiple Airlines
Deal found 10/21$335
This Delta deal was found by Cheapflights users on 10/19. 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 11/256:25 amBIL - MDW
1 stop5h 42mDelta
Tue 12/27:02 pmMDW - BIL
1 stop5h 46mDelta
Deal found 10/19$339
This Delta deal was found by Cheapflights users on 10/19. 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 11/236:25 amBIL - MDW
1 stop5h 42mDelta
Wed 12/31:50 pmMDW - BIL
1 stop10h 58mDelta
Deal found 10/19$354
This Delta deal was found by Cheapflights users on 10/19. 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 11/236:25 amBIL - MDW
1 stop5h 42mDelta
Fri 11/289:41 amMDW - BIL
2 stops9h 03mDelta
Deal found 10/19$369

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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(Kiwi.com)

One-way from

$132
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$278

Good round-trip deal

$374 or less

Good one-way deal

$259 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. 21% potential increase in price ($110 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 22, 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

Wed 11/19

5:18 am-12:38 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 11/26

7:40 pm-12:10 am

1 stop5h 30m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Thu 2/26

5:40 am-12:26 pm

1 stop5h 46m

Chicago O'Hare Intl

Mon 3/2

7:00 pm-10:50 pm

1 stop4h 50m

$249

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Sun 11/23

6:25 am-11:34 am

1 stop4h 09m

Chicago O'Hare Intl

Mon 12/1

3:52 pm-12:10 am

2 stops9h 18m

$254

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Thu 11/27

6:25 am-11:34 am

1 stop4h 09m

Chicago O'Hare Intl

Mon 12/1

5:42 pm-12:10 am

2 stops7h 28m

$254

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Thu 2/26

6:15 am-1:08 pm

1 stop5h 53m

Chicago Midway

Mon 3/2

6:45 pm-10:50 pm

1 stop5h 05m

$294

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sun 11/23

6:25 am-1:07 pm

1 stop5h 42m

Chicago Midway

Tue 12/2

7:02 pm-11:48 pm

1 stop5h 46m

$294

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Tue 11/25

5:18 am-4:52 pm

2 stops10h 34m

Chicago O'Hare Intl

Mon 12/1

3:52 pm-12:10 am

2 stops9h 18m

$320

BillingsChicago

BIL - ORD

BILORD

Billings Logan Intl

Sun 12/14

10:24 pm-8:17 pm

2 stops20h 53m

Chicago O'Hare Intl

Thu 12/18

9:33 pm-2:08 pm

1 stop17h 35m

$335

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sun 11/23

6:25 am-1:07 pm

1 stop5h 42m

Chicago Midway

Fri 11/28

9:41 am-5:44 pm

2 stops9h 03m

$369

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Fri 11/14

6:25 am-1:07 pm

1 stop5h 42m

Chicago Midway

Tue 11/18

7:02 pm-11:24 pm

1 stop5h 22m

$374

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 23 results
1
2
3

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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 February is currently the most expensive (average of $597). 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 October 22, 2025.

When flying from Billings to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 October 22, 2025.

The most flights from BIL to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).

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 October 22, 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
7,981 reviews

Boarding

8.2

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,981 reviews
Delta
7.9
Good
7,981 reviews

Boarding

8.2

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,988 reviews
Delta
7.9
Good
7,981 reviews

Boarding

8.2

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,029 reviews
Delta
7.9
Good
7,981 reviews

Boarding

8.2

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 2 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 20m. Billings and Chicago are separated by a distance of 1057 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 43% 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 (85%), Envoy Air (85%) and SkyWest Airlines (80%).

  • What are the cheapest flights from Billings to Chicago?

    Looking for the cheapest flight from Billings to Chicago? While on average our users pay $411, our data indicates the cheapest price to be $185. 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, 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 February is currently the most expensive (average of $597). 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
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Billings to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Bozeman to O'Hare Intl flights
Missoula to O'Hare Intl flights
Bozeman to St. Louis flights
Bozeman to Midway flights
Kalispell to O'Hare Intl flights
Billings to O'Hare Intl flights
Missoula to Midway flights
Missoula to St. Louis flights
Billings to Midway flights
Kalispell to Midway flights
Billings to Moline flights
Kalispell to St. Louis flights
Great Falls to O'Hare Intl flights
Helena to O'Hare Intl flights
Butte to O'Hare Intl flights
Billings to St. Louis flights
Cody to O'Hare Intl flights
Kalispell to Peoria flights
Missoula to Peoria flights
Helena to St. Louis flights
Helena to Midway flights
Great Falls to Midway flights
Billings to Evansville flights
Helena to Moline flights
Kalispell to Moline flights
Bozeman to Moline flights
Butte to St. Louis flights
Butte to Midway flights
Missoula to Moline flights
Bozeman to Dubuque flights
Cody to Springfield flights
Cody to Bloomington flights
Missoula to Dubuque flights

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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$371FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$427FlexibilityNo cancel feeOn-time69%
DeltaCheapest$248Average$391FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.