$170 Cheap Flights from Billings (BIL) to Chicago (MDW)

View $170 flight on Tue, Jan 20, 2026Opens in a new window

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

Cheap Flights from Billings to Chicago (BIL-MDW)

Prices were available within the past 7 days and start at $170 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Dec 15 - Wed, Jan 7
BIL
Billings
MDW
Chicago
$249 Roundtrip, found 21 hours ago
$249
Roundtrip
found 21 hours ago
Select Delta flight, departing Mon, Dec 15 from Billings to Chicago, returning Wed, Jan 7, priced at $249 found 21 hours ago
Delta
Wed, Dec 10 - Wed, Dec 17
BIL
Billings
MDW
Chicago
$254 Roundtrip, found 2 days ago
$254
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Dec 10 from Billings to Chicago, returning Wed, Dec 17, priced at $254 found 2 days ago
Delta
Mon, Dec 8 - Sat, Dec 13
BIL
Billings
MDW
Chicago
$259 Roundtrip, found 2 hours ago
$259
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Dec 8 from Billings to Chicago, returning Sat, Dec 13, priced at $259 found 2 hours ago
Delta
Fri, Apr 24 - Sat, May 9
BIL
Billings
MDW
Chicago
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Apr 24 from Billings to Chicago, returning Sat, May 9, priced at $264 found 1 day ago
Delta
Tue, Nov 4 - Mon, Nov 10
BIL
Billings
MDW
Chicago
$279 Roundtrip, found 2 days ago
$279
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Nov 4 from Billings to Chicago, returning Mon, Nov 10, priced at $279 found 2 days ago
Delta
Mon, Dec 15 - Mon, Jan 5
BIL
Billings
MDW
Chicago
$294 Roundtrip, found 21 hours ago
$294
Roundtrip
found 21 hours ago
Select Delta flight, departing Mon, Dec 15 from Billings to Chicago, returning Mon, Jan 5, priced at $294 found 21 hours ago
Delta
Thu, Nov 20 - Thu, Dec 4
BIL
Billings
MDW
Chicago
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Nov 20 from Billings to Chicago, returning Thu, Dec 4, priced at $299 found 1 day ago
Delta
Thu, Apr 16 - Fri, May 1
BIL
Billings
MDW
Chicago
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Apr 16 from Billings to Chicago, returning Fri, May 1, priced at $309 found 1 day ago
Delta
Mon, Apr 27 - Sat, May 9
BIL
Billings
MDW
Chicago
$310 Roundtrip, found 4 days ago
$310
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Apr 27 from Billings to Chicago, returning Sat, May 9, priced at $310 found 4 days ago
Delta
Wed, May 27 - Tue, Jun 16
BIL
Billings
MDW
Chicago
$314 Roundtrip, found 4 days ago
$314
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, May 27 from Billings to Chicago, returning Tue, Jun 16, priced at $314 found 4 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $334
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $334
Flights from Billings (BIL) to Chicago (MDW)
Origin airport
Logan Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$248
Distance
1070 mi

Billings to Chicago Flights

The cheapest times to fly from Billings to Chicago

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 Billings to Chicago are during the month of December. You can find some of the cheapest flights from Billings to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Billings to Chicago

Sunday is one of the best days to book for cheap flights from Billings to Chicago: 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 Billings to Chicago

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 Billings to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $170 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 Billings to Chicago 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 Billings to Chicago 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 Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $170 or cheap return flight from $249 from Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW)?
The cheapest month to fly from BIL to MDW is December, when demand is low. Off-peak season is generally when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest BIL to MDW flight.
How many flights per day from Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights departing from Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from BIL to MDW?
Typically you'll find the widest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can change depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW) route, travel before 3 PM. Departures after this time have a 22% higher chance of being canceled.**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 Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW) last-minute?
Holding off until right before your break to book your flight from BIL to MDW generally means paying more. While you might find some last-minute deals, there's no guarantee. Be flexible with your travel plans for the best chance of scoring a bargain.
Is it cheaper to book a BIL to MDW flight and hotel package?
You'll generally save money by booking a BIL to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. Once you've chosen your preferred flights and accommodations, consider adding extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Logan Intl. Airport (BIL) to Midway Intl. Airport (MDW)?
Typically, it's possible to reschedule or cancel your BIL to MDW flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.