$105 Cheap Flights from Bozeman (BZN) to Chicago (MDW)

View $105 flight on Sun, Dec 14, 2025Opens in a new window

Popular airlines from Bozeman Yellowstone Intl. Airport (BZN) to Chicago Midway Airport (MDW)

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Cheap Flights from Bozeman to Chicago (BZN-MDW)

Prices were available within the past 7 days and start at $105 for one-way flights and $209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Jan 6 - Sat, Jan 10
BZN
Bozeman
MDW
Chicago
$209 Roundtrip, found 2 hours ago
$209
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Jan 6 from Bozeman to Chicago, returning Sat, Jan 10, priced at $209 found 2 hours ago
Delta
Sat, Dec 13 - Wed, Dec 24
BZN
Bozeman
MDW
Chicago
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Dec 13 from Bozeman to Chicago, returning Wed, Dec 24, priced at $217 found 1 hour ago
Delta
Wed, Feb 4 - Sun, Feb 8
BZN
Bozeman
MDW
Chicago
$218 Roundtrip, found 2 days ago
$218
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Feb 4 from Bozeman to Chicago, returning Sun, Feb 8, priced at $218 found 2 days ago
Southwest Airlines
Wed, Feb 4 - Sun, Feb 8
BZN
Bozeman
MDW
Chicago
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Feb 4 from Bozeman to Chicago, returning Sun, Feb 8, priced at $219 found 2 days ago
Southwest Airlines
Sat, Dec 13 - Wed, Dec 24
BZN
Bozeman
MDW
Chicago
$224 Roundtrip, found 1 hour ago
$224
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Bozeman to Chicago, returning Wed, Dec 24, priced at $224 found 1 hour ago
Southwest Airlines
Thu, Feb 5 - Tue, Feb 10
BZN
Bozeman
MDW
Chicago
$224 Roundtrip, found 4 days ago
$224
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Feb 5 from Bozeman to Chicago, returning Tue, Feb 10, priced at $224 found 4 days ago
Southwest Airlines
Mon, Jan 26 - Thu, Jan 29
BZN
Bozeman
MDW
Chicago
$243 Roundtrip, found 6 days ago
$243
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Jan 26 from Bozeman to Chicago, returning Thu, Jan 29, priced at $243 found 6 days ago
Delta
Wed, Jan 28 - Sun, Feb 1
BZN
Bozeman
MDW
Chicago
$248 Roundtrip, just found
$248
Roundtrip
just found
Select Delta flight, departing Wed, Jan 28 from Bozeman to Chicago, returning Sun, Feb 1, priced at $248 just found
Southwest Airlines
Sun, Dec 7 - Tue, Dec 9
BZN
Bozeman
MDW
Chicago
$250 Roundtrip, found 2 hours ago
$250
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sun, Dec 7 from Bozeman to Chicago, returning Tue, Dec 9, priced at $250 found 2 hours ago
Southwest Airlines
Sat, Dec 13 - Wed, Dec 24
BZN
Bozeman
MDW
Chicago
$254 Roundtrip, found 1 hour ago
$254
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Bozeman to Chicago, returning Wed, Dec 24, priced at $254 found 1 hour 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 $315
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $315

Frequently asked questions

How much does a flight from Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $105 or cheap return flight from $209 from Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW) 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 Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW)?
Traveling in January is a great way to save, as it's the cheapest month for flights between BZN and MDW. You'll often find the lowest fares during the off-season.
What is the cheapest airline that flies from Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from BZN to MDW, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW)?
Direct flights from Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from BZN to MDW?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on a number of factors, including the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from BZN to MDW?
With 91% of journeys typically arriving on schedule, Southwest Airlines has the best on-time performance for nonstop flights from Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW). To check your flight status and receive notifications if anything changes, head to the Expedia App.
What is the best time to fly from Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW) route, aim to fly before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**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.
What airports do you fly into for Chicago from Gallatin Field Airport (BZN)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Gallatin Field Airport (BZN). Check out the available options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from BZN to MDW are typically more expensive. To secure the cheapest rates, start searching for flights well ahead of time. That said, if you're flexible with your travel plans, you may score a cheap fare right before your journey.
Is it cheaper to book a BZN to MDW flight and hotel package?
You'll generally save money by booking a BZN to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. Once you've chosen your ideal accommodations and flights, consider other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Gallatin Field Airport (BZN) to Midway Intl. Airport (MDW)?
Typically, you're able to cancel or reschedule your BZN to MDW flight. However, additional charges may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you'd like further details, go to our Customer Service portal.

Travel information

Origin airport
Bozeman Yellowstone Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$208
Distance
1195 mi

Book with confidence

Bozeman to Chicago Flights

The cheapest times to fly from Bozeman 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 Bozeman to Chicago are during the month of January. You can find some of the cheapest flights from Bozeman to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Bozeman to Chicago

Sunday is one of the best days to book for cheap flights from Bozeman 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 Bozeman 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 Bozeman to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $105 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 Bozeman 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 Bozeman 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.

 

Bozeman to Chicago Flights

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