$167 Cheap Flights from Chicago (MDW) to Billings (BIL)

View $167 flight on Tue, Jan 20, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Billings Logan Intl. Airport (BIL)

Cheap Flights from Chicago to Billings (MDW-BIL)

Prices were available within the past 7 days and start at $167 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jan 20 - Mon, Feb 9
MDW
Chicago
BIL
Billings
$249 Roundtrip, found 8 hours ago
$249
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Jan 20 from Chicago to Billings, returning Mon, Feb 9, priced at $249 found 8 hours ago
Delta
Wed, Jan 21 - Mon, Jan 26
MDW
Chicago
BIL
Billings
$254 Roundtrip, found 16 hours ago
$254
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Jan 21 from Chicago to Billings, returning Mon, Jan 26, priced at $254 found 16 hours ago
Delta
Sat, Jan 10 - Sat, Jan 24
MDW
Chicago
BIL
Billings
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jan 10 from Chicago to Billings, returning Sat, Jan 24, priced at $259 found 1 day ago
Delta
Sun, Jan 18 - Mon, Feb 2
MDW
Chicago
BIL
Billings
$270 Roundtrip, found 1 day ago
$270
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jan 18 from Chicago to Billings, returning Mon, Feb 2, priced at $270 found 1 day ago
Delta
Thu, Jan 29 - Fri, Feb 13
MDW
Chicago
BIL
Billings
$274 Roundtrip, just found
$274
Roundtrip
just found
Select Delta flight, departing Thu, Jan 29 from Chicago to Billings, returning Fri, Feb 13, priced at $274 just found
Delta
Sun, Jan 4 - Sat, Jan 24
MDW
Chicago
BIL
Billings
$275 Roundtrip, found 1 day ago
$275
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jan 4 from Chicago to Billings, returning Sat, Jan 24, priced at $275 found 1 day ago
Delta
Thu, Jan 22 - Mon, Jan 26
MDW
Chicago
BIL
Billings
$279 Roundtrip, found 16 hours ago
$279
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Jan 22 from Chicago to Billings, returning Mon, Jan 26, priced at $279 found 16 hours ago
Delta
Sun, Jan 25 - Fri, Jan 30
MDW
Chicago
BIL
Billings
$291 Roundtrip, found 8 hours ago
$291
Roundtrip
found 8 hours ago
Select Delta flight, departing Sun, Jan 25 from Chicago to Billings, returning Fri, Jan 30, priced at $291 found 8 hours ago
Delta
Thu, Jan 29 - Wed, Feb 18
MDW
Chicago
BIL
Billings
$295 Roundtrip, found 1 day ago
$295
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jan 29 from Chicago to Billings, returning Wed, Feb 18, priced at $295 found 1 day ago
Delta
Fri, Jan 23 - Fri, Feb 13
MDW
Chicago
BIL
Billings
$304 Roundtrip, just found
$304
Roundtrip
just found
Select Delta flight, departing Fri, Jan 23 from Chicago to Billings, returning Fri, Feb 13, priced at $304 just found

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Alternative airports near Billings

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Logan Intl. BIL. Cheapest and Closest option available. Average driving time to city center is 5 minutes. Flights from $451
BIL
Logan Intl.
CheapestClosest
Average driving time to city center5 min
Flights from $451
Flights from Chicago (MDW) to Billings (BIL)
Origin airport
Midway Intl.
Destination airport
Logan Intl.
Airlines serving
Delta
Roundtrip price
$248
Distance
1070 mi

Chicago to Billings Flights

The cheapest times to fly from Chicago to Billings

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Billings are during the month of January. You can find some of the cheapest flights from Chicago to Billings with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Billings

Sunday is one of the best days to book for cheap flights from Chicago to Billings: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Billings

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Billings in 2025. You can also book with separate airlines for your outbound and return journeys, from $167 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Billings flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Billings airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Logan Intl. Airport (BIL) cost?
Get a cheap one-way flight from $167 or cheap return flight from $249 from Midway Intl. Airport (MDW) to Logan Intl. Airport (BIL) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Logan Intl. Airport (BIL)?
Flying in January can help you save, as it's the cheapest month for flights between MDW and BIL. You'll often find the lowest fares during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Logan Intl. Airport (BIL)?
To find the cheapest airline that'll fly you from MDW to BIL, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Midway Intl. Airport (MDW) to Logan Intl. Airport (BIL)?
Direct flights from Midway Intl. Airport (MDW) to Logan Intl. Airport (BIL) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to BIL?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can vary based on a range of factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Logan Intl. Airport (BIL)?
To arrive at Logan Intl. Airport (BIL) on schedule, book a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Logan Intl. Airport (BIL) last-minute?
Last-minute fares from MDW to BIL are typically more expensive. To secure the lowest rates, start looking for flights as soon as possible. That said, if you're flexible with your travel dates, you may score a cheap ticket just before your departure.
Is it cheaper to book a MDW to BIL flight and hotel package?
Securing a MDW to BIL flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Choose from our impressive range of stays and then add flights, activities and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Logan Intl. Airport (BIL)?
In most cases, you can cancel or reschedule your MDW to BIL flight. However, additional charges may apply, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like more information, visit our Customer Service portal.

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*Available to One Key members.