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$157+ Cheap flights from Chicago (CHI) to Billings (BIL)

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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BIL
Aug 7 — Aug 141
Thu 8/7
Thu 8/14
1 adult, Economy
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Cheap flight deals from Chicago to Billings

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Billings (BIL). 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 August 2, 2025.

Round-trip from

$229
(American Airlines)

One-way from

$157
(Alaska Airlines)

Popular in

September

Cheapest in

May

Average price

$452

Good round-trip deal

$315 or less
From Chicago (CHI) to Billings Logan Intl
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One-way flight from Chicago (CHI) to Billings Logan Intl
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Highest demand for flights based on searches. 16% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 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 Chicago (CHI) to Billings Logan Intl.
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Find flight deals from Chicago to Billings

Cheapest flights from Chicago to Billings
Explore the most affordable flight options available from Chicago to Billings. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2025.

This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:50 pmORD - BIL
Nonstop3h 07mAmerican Airlines
Tue 9/96:02 amBIL - ORD
Nonstop2h 53mAmerican Airlines
Deal found 8/1$229
This United Airlines deal was found by Cheapflights users on 7/31. 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 8/238:55 amORD - BIL
Nonstop3h 21mUnited Airlines
Sat 8/302:35 pmBIL - ORD
1 stop5h 05mUnited Airlines
Deal found 7/31$239
This Delta deal was found by Cheapflights users on 8/1. 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.
Sat 9/271:43 pmMDW - BIL
1 stop7h 01mDelta
Tue 9/306:25 amBIL - MDW
1 stop5h 38mDelta
Deal found 8/1$249
This Delta deal was found by Cheapflights users on 8/1. 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.
Sat 9/279:50 amORD - BIL
2 stops10h 54mDelta
Tue 9/305:25 amBIL - ORD
1 stop5h 28mDelta
Deal found 8/1$254
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1110:27 amORD - BIL
2 stops23h 41mMultiple Airlines
Mon 9/159:33 pmBIL - ORD
2 stops14h 36mMultiple Airlines
Deal found 7/31$313
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/121:01 pmORD - BIL
1 stop12h 10mAlaska Airlines
Thu 9/182:04 pmBIL - ORD
1 stop8h 59mAlaska Airlines
Deal found 7/31$372
This Hawaiian Airlines deal was found by Cheapflights users on 7/31. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:00 amORD - BIL
1 stop10h 04mHawaiian Airlines
Sun 10/197:15 pmBIL - ORD
1 stop10h 09mHawaiian Airlines
Deal found 7/31$382

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Billings 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 August 2, 2025.
Use the filters below to find and compare flights from Chicago to Billings that are best for you.

Fly from

Chicago

Fly to

Billings

Route

Depart

Return

Price

ChicagoBillings

ORD - BIL

ORDBIL

Chicago O'Hare Intl

Thu 9/4

6:50 pm-8:57 pm

Nonstop3h 07m

Billings Logan Intl

Tue 9/9

6:02 am-9:55 am

Nonstop2h 53m

$229

ChicagoBillings

ORD - BIL

ORDBIL

Chicago O'Hare Intl

Sat 8/23

8:55 am-11:16 am

Nonstop3h 21m

Billings Logan Intl

Sat 8/30

2:35 pm-8:40 pm

1 stop5h 05m

$239

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Sat 9/27

1:43 pm-7:44 pm

1 stop7h 01m

Billings Logan Intl

Tue 9/30

6:25 am-1:03 pm

1 stop5h 38m

$249

ChicagoBillings

ORD - BIL

ORDBIL

Chicago O'Hare Intl

Sat 9/27

9:50 am-7:44 pm

2 stops10h 54m

Billings Logan Intl

Tue 9/30

5:25 am-11:53 am

1 stop5h 28m

$254

ChicagoBillings

ORD - BIL

ORDBIL

Chicago O'Hare Intl

Thu 9/11

10:27 am-9:08 am

2 stops23h 41m

Billings Logan Intl

Mon 9/15

9:33 pm-1:09 pm

2 stops14h 36m

$313

ChicagoBillings

ORD - BIL

ORDBIL

Chicago O'Hare Intl

Fri 9/12

1:01 pm-12:11 am

1 stop12h 10m

Billings Logan Intl

Thu 9/18

2:04 pm-12:03 am

1 stop8h 59m

$372

ChicagoBillings

ORD - BIL

ORDBIL

Chicago O'Hare Intl

Wed 10/15

6:00 am-3:04 pm

1 stop10h 04m

Billings Logan Intl

Sun 10/19

7:15 pm-6:24 am

1 stop10h 09m

$382

ChicagoBillings

ORD - BIL

ORDBIL

Chicago O'Hare Intl

Sat 9/27

8:00 am-3:03 pm

1 stop8h 03m

$157

ChicagoBillings

ORD - BIL

ORDBIL

Chicago O'Hare Intl

Sat 8/30

6:24 pm-11:02 pm

1 stop5h 38m

$158

ChicagoBillings

ORD - BIL

ORDBIL

Chicago O'Hare Intl

Sun 8/31

9:45 am-11:49 am

Nonstop3h 04m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 14 results
1
2

Best time to book a flight from Chicago to Billings

Have a flexible travel schedule? Discover the best time to fly to Billings from Chicago 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 Chicago to Billings

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

Find hourly flight availability from Chicago to Billings. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Billings in the evening. If you’re flexible enough to do this you can expect to save up to 50% on your trip compared to booking a flight at noon.

Weekly flight availability from Chicago to Billings

Explore weekly flight availability from Chicago to Billings. 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 August 2, 2025.

The most flights from CHI to BIL are scheduled on a Monday (4 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Billings

Get insights into the airlines that provide service to Billings. 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 Billings. Reviews last updated August 2, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Chicago to Billings to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,983 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,613 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,904 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

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

    For a flight from Chicago to Billings, you will be flying into Billings Logan Intl. Billings Logan Intl (BIL) is just 2.7 mi from the center of the city. Billings Logan Intl is the only Billings airport and it handles 3 inbound flights from Chicago per day. 3 airlines have flights to Billings Logan Intl from Chicago on a regular basis.

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

    Our cheapest airline available from Chicago to Billings is American Airlines. Our recent data shows that you can find tickets from as low as $229 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $239 and $249 round-trip. These flights start at 52% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Billings one-way?

    The cheapest airlines for a one-way flight from Chicago to Billings are Alaska Airlines ($157), Delta ($158), and American Airlines ($176).

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

    The top 3 most reliable airlines when flying from Chicago to Billings are American Airlines (71%), Envoy Air (71%) and Qatar Airways (69%).

  • What are the cheapest flights from Chicago to Billings?

    While on average a flight from Chicago to Billings is generally $414, our data shows the cheapest flight currently is $229. When looking at the most popular route, (Chicago O'Hare Intl - Billings Logan Intl), you can expect to pay $239 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Billings 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 Chicago to Billings?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Billings (average of $395). Flying from Chicago to Billings in June is currently the most expensive (average of $512). 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

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Alternative routes for Chicago to Billings

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Top 3 airlines flying from Chicago to Billings

Discover the top 3 airlines that operate flights from Chicago to Billings. 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 August 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$334FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$294Average$470FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$306Average$462FlexibilityNo cancel feeOn-time69%

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