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

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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — MDW
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Find flight deals from Billings to Midway

Cheapest flights from Billings to Midway
Explore the most affordable flight options available from Billings to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2025.

This Delta deal was found by Cheapflights users on 11/19. 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 12/46:25 amBIL - MDW
1 stop5h 45mDelta
Mon 12/87:02 pmMDW - BIL
1 stop5h 46mDelta
Deal found 11/19$299
This Delta deal was found by Cheapflights users on 11/20. 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.
Tue 11/256:25 amBIL - MDW
1 stop5h 42mDelta
Mon 12/157:02 pmMDW - BIL
1 stop5h 46mDelta
Deal found 11/20$379
This Delta deal was found by Cheapflights users on 11/19. 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 11/2711:42 amBIL - MDW
2 stops10h 58mDelta
Mon 12/17:02 pmMDW - BIL
1 stop5h 22mDelta
Deal found 11/19$404
This Delta deal was found by Cheapflights users on 11/20. 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.
Fri 12/196:25 amBIL - MDW
1 stop5h 45mDelta
Tue 12/305:59 pmMDW - BIL
1 stop6h 20mDelta
Deal found 11/20$499
This Delta deal was found by Cheapflights users on 11/20. 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.
Fri 12/56:25 amBIL - MDW
1 stop5h 45mDelta
Sun 12/77:02 pmMDW - BIL
1 stop5h 46mDelta
Deal found 11/20$606
This Delta deal was found by Cheapflights users on 11/20. 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.
Sat 12/205:15 amBIL - MDW
2 stops11h 04mDelta
Sat 12/275:59 pmMDW - BIL
1 stop6h 20mDelta
Deal found 11/20$618
This Delta deal was found by Cheapflights users on 11/19. 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 12/305:14 amBIL - MDW
2 stops11h 12mDelta
Sun 1/45:59 pmMDW - BIL
1 stop6h 20mDelta
Deal found 11/19$719

Cheap flight deals from Billings to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Billings (BIL) to Midway (MDW). 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 November 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$249
(Delta)

Popular in

November

Cheapest in

January

Average price

$654
Provider with most accurate pricing for Billings Logan Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Billings Logan Intl-Chicago Midway flights.
Search Deals
From Billings Logan Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($93 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 November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Billings to Midway 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 November 20, 2025.
Use the filters below to find and compare flights from Billings to Chicago Midway Airport that are best for you.

Fly from

Billings

Fly to

Midway

Route

Depart

Return

Price

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Thu 1/22

6:10 am-1:09 pm

1 stop5h 59m

Chicago Midway

Sun 1/25

1:49 pm-7:24 pm

1 stop6h 35m

$249

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Thu 2/26

6:10 am-1:09 pm

1 stop5h 59m

Chicago Midway

Mon 3/2

1:49 pm-7:36 pm

1 stop6h 47m

$249

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Thu 3/26

6:15 am-1:08 pm

1 stop5h 53m

Chicago Midway

Mon 3/30

6:45 pm-10:50 pm

1 stop5h 05m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Compare providers for flights from Billings to Midway

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 Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

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

Have a flexible travel schedule? Discover the best time to fly to Midway 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 20, 2025.
Get a feel of what it's like to fly with Delta from Billings to Chicago Midway Airport 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
8,002 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.1

Overall

7.9

Crew

8.5

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
8,002 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.1

Overall

7.9

Crew

8.5

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 Midway. 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 Midway?

    Billings Logan Intl (BIL) is the airport you will fly out of if you book a flight from Billings to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Billings Logan Intl; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Billings airport to Chicago Midway. It is only a 2.7 mi journey to Billings Logan Intl (BIL) from Billings’s city center.

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

    A quick flight from Billings to Chicago Midway Airport can take about 5h 59m. Delta provides one of the quickest options available for as low as $249. The distance between Billings and Chicago Midway Airport is about 1070 mi.

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

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

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

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

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

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

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Top airline flying from Billings to Midway

Discover the top airline that operate flights from Billings to Midway. 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$328Average$616FlexibilityNo cancel feeOn-timeN/A

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