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$186+ Cheap flights from Midway (MDW) 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BIL
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$291
(Delta)

One-way from

$186
(Delta)

Popular in

March

Cheapest in

October

Average price

$564
Provider with most accurate pricing for Chicago Midway-Billings Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Billings Logan Intl flights.
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From Chicago Midway to Billings Logan Intl
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One-way flight from Chicago Midway to Billings Logan Intl
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Highest demand for flights based on searches. 14% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 12, 2025.

This Delta deal was found by Cheapflights users on 11/12. 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
Tue 12/166:25 amBIL - MDW
1 stop5h 45mDelta
Deal found 11/12$291
This Delta deal was found by Cheapflights users on 11/11. 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 12/312:50 pmMDW - BIL
2 stops11h 58mDelta
Sun 12/76:25 amBIL - MDW
1 stop5h 45mDelta
Deal found 11/11$348
This Delta deal was found by Cheapflights users on 11/10. 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 12/47:02 pmMDW - BIL
1 stop5h 46mDelta
Mon 12/86:25 amBIL - MDW
1 stop5h 45mDelta
Deal found 11/10$353
This Delta deal was found by Cheapflights users on 11/11. 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 12/117:02 pmMDW - BIL
1 stop5h 46mDelta
Sun 12/146:25 amBIL - MDW
1 stop5h 45mDelta
Deal found 11/11$405
This Delta deal was found by Cheapflights users on 11/11. 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 11/1812:47 pmMDW - BIL
2 stops11h 37mDelta
Thu 12/46:25 amBIL - MDW
1 stop5h 45mDelta
Deal found 11/11$496

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 November 12, 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

Mon 12/8

7:02 pm-11:48 pm

1 stop5h 46m

Billings Logan Intl

Tue 12/16

6:25 am-6:00 pm

2 stops10h 35m

$296

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Fri 1/2

5:59 pm-11:19 pm

1 stop6h 20m

Billings Logan Intl

Tue 1/6

6:22 am-1:09 pm

1 stop5h 47m

$322

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Wed 12/3

12:50 pm-11:48 pm

2 stops11h 58m

Billings Logan Intl

Sun 12/7

6:25 am-1:10 pm

1 stop5h 45m

$348

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Thu 12/4

7:02 pm-11:48 pm

1 stop5h 46m

Billings Logan Intl

Mon 12/8

6:25 am-1:10 pm

1 stop5h 45m

$353

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Wed 4/22

2:00 pm-8:07 pm

1 stop7h 07m

Billings Logan Intl

Sat 4/25

6:15 am-1:07 pm

1 stop5h 52m

$356

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Thu 1/1

5:59 pm-11:19 pm

1 stop6h 20m

Billings Logan Intl

Mon 1/5

6:22 am-1:09 pm

1 stop5h 47m

$396

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Mon 12/15

7:02 pm-11:48 pm

1 stop5h 46m

$186

ChicagoBillings

MDW - BIL

MDWBIL

Chicago Midway

Mon 12/15

8:42 pm-2:56 pm

3 stops43h 14m

$403

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 Chicago Midway Airport-Billings flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Billings flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

How often are flights from Chicago to Billings delayed?

About 33% of weekly flights between Chicago and Billings have experienced delays in the past year, with the average delay time being 40 minutes.

What is the most punctual flight time for Chicago to Billings flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Monday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

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 46m. Delta provides one of the quickest options available for as low as $296. 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.

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