HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Billings

$249+ Cheap flights from Midway (MDW) to Billings (BIL)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BIL
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Billings 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.

Cheap flight deals from Midway to Billings

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(Delta)

Popular in

March

Cheapest in

August

Average price

$404
Provider with most accurate pricing for Chicago Midway-Billings Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Billings Logan Intl flights.
Search Deals
From Chicago Midway to Billings Logan Intl
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Midway to Billings

Cheapest flights from Midway to Billings
Explore the most affordable flight options available from Midway to Billings. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2025.

This Delta deal was found by Cheapflights users on 9/27. 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 10/253:00 pmMDW - BIL
1 stop5h 42mDelta
Sat 11/16:25 amBIL - MDW
1 stop5h 43mDelta
Deal found 9/27$249
This Delta deal was found by Cheapflights users on 9/27. 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 11/1112:47 pmMDW - BIL
2 stops12h 23mDelta
Tue 11/185:18 amBIL - MDW
2 stops11h 50mDelta
Deal found 9/27$259
This Delta deal was found by Cheapflights users on 9/29. 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.
Mon 10/277:10 pmMDW - BIL
1 stop5h 08mDelta
Mon 11/36:25 amBIL - MDW
1 stop5h 43mDelta
Deal found 9/29$294
This Delta deal was found by Cheapflights users on 9/28. 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.
Mon 12/87:02 pmMDW - BIL
1 stop5h 46mDelta
Thu 12/115:14 amBIL - MDW
2 stops11h 46mDelta
Deal found 9/28$296
This Delta deal was found by Cheapflights users on 9/27. 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 11/1312:47 pmMDW - BIL
2 stops12h 23mDelta
Tue 11/186:25 amBIL - MDW
1 stop5h 42mDelta
Deal found 9/27$315
This Delta deal was found by Cheapflights users on 9/27. 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 11/141:15 pmMDW - BIL
2 stops11h 55mDelta
Tue 11/185:18 amBIL - MDW
2 stops10h 20mDelta
Deal found 9/27$374
This Delta deal was found by Cheapflights users on 9/28. 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.
Mon 9/297:15 pmMDW - BIL
1 stop4h 55mDelta
Mon 10/66:25 amBIL - MDW
1 stop5h 43mDelta
Deal found 9/28$424

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 September 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Billings that are best for you.

Fly from

Midway

Fly to

Billings

Route

Depart

Return

Price

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Sat 10/25

3:00 pm-7:42 pm

1 stop5h 42m

Billings Logan Intl

Sat 11/1

6:25 am-1:08 pm

1 stop5h 43m

$249

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Sat 2/21

6:45 pm-10:50 pm

1 stop5h 05m

Billings Logan Intl

Sat 2/28

6:15 am-1:08 pm

1 stop5h 53m

$249

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Fri 11/14

7:02 pm-11:25 pm

1 stop5h 23m

Billings Logan Intl

Tue 11/18

6:25 am-1:07 pm

1 stop5h 42m

$249

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Sat 11/22

7:02 pm-11:24 pm

1 stop5h 22m

Billings Logan Intl

Thu 11/27

11:42 am-11:40 pm

2 stops10h 58m

$254

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Mon 10/27

7:10 pm-11:18 pm

1 stop5h 08m

Billings Logan Intl

Mon 11/3

6:25 am-4:14 pm

2 stops8h 49m

$254

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Tue 11/11

7:02 pm-11:24 pm

1 stop5h 22m

Billings Logan Intl

Tue 11/18

5:18 am-6:08 pm

2 stops11h 50m

$254

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Sun 10/5

7:15 pm-11:38 pm

1 stop5h 23m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Compare providers for flights from Midway to Billings

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 Midway to Billings in September.
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 Chicago Midway Airport-Billings flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Billings flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Billings flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Billings 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 Chicago Midway Airport-Billings 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 Midway to Billings

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

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

Find hourly flight availability from Midway 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 September 29, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway?

    Most people fly into Billings Logan Intl (BIL) if they book a flight to Billings from Chicago Midway. On average, Billings Logan Intl has 0 inbound flights from Chicago Midway per day from 0 airlines. Billings Logan Intl is conveniently located just 2.7 mi from Billings’s city center.

  • How long is the flight from Chicago Midway Airport to Billings?

    A quick flight from Chicago Midway Airport to Billings can take about 5h 42m. Delta provides one of the quickest options available for as low as $249. There are 1070 mi between Chicago Midway Airport and Billings.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to Billings?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Billings (average of $396). Flying from Chicago Midway Airport to Billings in June is currently the most expensive (average of $507). 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

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.

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.