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Cheap flights from Montana to Chicago from $105

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montana to Chicago departing on 3/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Montana to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:25 am - 1:25 pm
BIL
-
MDW
6h 00m
1 stop
Delta Logo
2:05 pm - 8:19 pm
MDW
-
BIL
7h 14m
1 stop
$209Delta
Tue, Mar 31 - Sat, Apr 4
Delta Logo
6:25 am - 5:54 pm
BIL
-
MDW
10h 29m
2 stops
Delta Logo
2:05 pm - 8:19 pm
MDW
-
BIL
7h 14m
1 stop
$214Delta
Tue, Mar 31 - Sat, Apr 4
Delta Logo
2:53 pm - 10:28 pm
BZN
-
MDW
6h 35m
1 stop
Delta Logo
2:12 pm - 8:11 pm
MDW
-
BZN
6h 59m
1 stop
$217Delta
Thu, Apr 23 - Sat, Apr 25
Southwest Logo
2:55 pm - 9:20 pm
BZN
-
MDW
5h 25m
1 stop
Southwest Logo
6:10 pm - 12:15 am
MDW
-
BZN
7h 05m
1 stop
$229Southwest
Sat, Apr 25 - Tue, May 5
Delta Logo
2:53 pm - 10:28 pm
BZN
-
MDW
6h 35m
1 stop
Delta Logo
6:00 am - 1:36 pm
MDW
-
BZN
8h 36m
1 stop
$249Delta
Thu, Apr 23 - Sat, Apr 25
Southwest Logo
11:20 am - 9:30 pm
BZN
-
MDW
9h 10m
1 stop
Southwest Logo
5:30 pm - 9:40 pm
MDW
-
BZN
5h 10m
1 stop
$251Southwest
Wed, Apr 8 - Sat, Apr 11
Delta Logo
2:53 pm - 10:28 pm
BZN
-
MDW
6h 35m
1 stop
Delta Logo
2:12 pm - 8:11 pm
MDW
-
BZN
6h 59m
1 stop
$258Delta
Wed, Apr 15 - Fri, Apr 17
Delta Logo
5:20 am - 5:54 pm
BZN
-
MDW
11h 34m
2 stops
Delta Logo
2:05 pm - 8:14 pm
MDW
-
BZN
7h 09m
1 stop
$263Delta
Wed, Mar 25 - Thu, Mar 26
Delta Logo
2:53 pm - 10:28 pm
BZN
-
MDW
6h 35m
1 stop
Delta Logo
6:00 am - 1:36 pm
MDW
-
BZN
8h 36m
1 stop
$264Delta
Fri, Apr 17 - Sun, Apr 19
Southwest Logo
7:30 am - 5:15 pm
BZN
-
MDW
8h 45m
2 stops
Southwest Logo
6:30 am - 10:40 am
MDW
-
BZN
5h 10m
1 stop
$270Southwest
Sat, Apr 18 - Tue, Apr 28

Delta flights from Montana to Chicago Midway Airport

Our best Delta deals on Montana to Chicago Midway Airport flight tickets
Delta
Mar 31
BIL6:25 amBillings Logan Intl
6h 00m
1 stop
MDW1:25 pmChicago Midway
Apr 4
MDW2:05 pmChicago Midway
7h 14m
1 stop
BIL8:19 pmBillings Logan Intl
$209
Delta
Mar 31
BIL6:25 amBillings Logan Intl
10h 29m
2 stops
MDW5:54 pmChicago Midway
Apr 4
MDW2:05 pmChicago Midway
7h 14m
1 stop
BIL8:19 pmBillings Logan Intl
$214
Delta
Apr 23
BZN2:53 pmBozeman Gallatin Field
6h 35m
1 stop
MDW10:28 pmChicago Midway
Apr 25
MDW2:12 pmChicago Midway
6h 59m
1 stop
BZN8:11 pmBozeman Gallatin Field
$217

Southwest flights from Montana to Chicago Midway Airport

Our best Southwest deals on Montana to Chicago Midway Airport flight tickets
Southwest
Apr 25
BZN2:55 pmBozeman Gallatin Field
5h 25m
1 stop
MDW9:20 pmChicago Midway
May 5
MDW6:10 pmChicago Midway
7h 05m
1 stop
BZN12:15 amBozeman Gallatin Field
$229
Southwest
Apr 8
BZN11:20 amBozeman Gallatin Field
9h 10m
1 stop
MDW9:30 pmChicago Midway
Apr 11
MDW5:30 pmChicago Midway
5h 10m
1 stop
BZN9:40 pmBozeman Gallatin Field
$251
Southwest
Apr 18
BZN7:30 amBozeman Gallatin Field
8h 45m
2 stops
MDW5:15 pmChicago Midway
Apr 28
MDW6:30 amChicago Midway
5h 10m
1 stop
BZN10:40 amBozeman Gallatin Field
$270

momondo Fare Finder

 
Customize your flight search to find flights from Montana to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated February 25, 2026.
Use the filters below to find and compare flights from Montana to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Tue 3/31

6:25 am-1:25 pm

1 stop6h 00m

Chicago Midway

Sat 4/4

2:05 pm-8:19 pm

1 stop7h 14m

$209

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Tue 3/31

6:25 am-5:54 pm

2 stops10h 29m

Chicago Midway

Sat 4/4

2:05 pm-8:19 pm

1 stop7h 14m

$214

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Thu 4/23

2:53 pm-10:28 pm

1 stop6h 35m

Chicago Midway

Sat 4/25

2:12 pm-8:11 pm

1 stop6h 59m

$217

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Sat 4/25

2:55 pm-9:20 pm

1 stop5h 25m

Chicago Midway

Tue 5/5

6:10 pm-12:15 am

1 stop7h 05m

$229

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Thu 4/23

2:53 pm-10:28 pm

1 stop6h 35m

Chicago Midway

Sat 4/25

6:00 am-1:36 pm

1 stop8h 36m

$249

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Wed 4/8

11:20 am-9:30 pm

1 stop9h 10m

Chicago Midway

Sat 4/11

5:30 pm-9:40 pm

1 stop5h 10m

$251

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Wed 4/15

2:53 pm-10:28 pm

1 stop6h 35m

Chicago Midway

Fri 4/17

2:12 pm-8:11 pm

1 stop6h 59m

$258

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Wed 3/25

5:20 am-5:54 pm

2 stops11h 34m

Chicago Midway

Thu 3/26

2:05 pm-8:14 pm

1 stop7h 09m

$263

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Fri 4/17

2:53 pm-10:28 pm

1 stop6h 35m

Chicago Midway

Sun 4/19

6:00 am-1:36 pm

1 stop8h 36m

$264

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Sat 4/18

7:30 am-5:15 pm

2 stops8h 45m

Chicago Midway

Tue 4/28

6:30 am-10:40 am

1 stop5h 10m

$270

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Montana to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Montana. The lowest ticket price found for a Thursday departure recently was $292. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Montana because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $518.

What is the cheapest Montana to Chicago Midway flight route?

Fly from Bozeman Gallatin Field to Chicago Midway for the best Montana - Chicago Midway flight prices

What cabin class options are available on Montana to Chicago Midway flights?

There is only 1 cabin class available to choose from on Montana to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Montana to Chicago Midway Airport flights?

You could potentially save up to 55% on your flight if you consider stops on a Montana to Chicago Midway Airport flight.

Cheap Montana to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montana to Chicago Midway Airport

Fastest flight time

2h 50m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun
The fastest flight from Montana to Chicago Midway Airport takes 2h 50m
Direct flights go from Montana to Chicago Midway Airport on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • When did momondo last update prices for flights from Montana to Chicago Midway Airport?

    Prices for flights from Montana to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Montana to Chicago Midway Airport?

  • How old do you have to be to fly from Montana to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Montana to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Montana to Chicago Midway Airport?

Best airlines flying from Montana to Chicago Midway Airport

Compare and see reviews for airlines that fly from Montana to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $249Free CancellationRating
7.9
8,237 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Montana to Chicago?

It is quick and easy to find Montana to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Montana to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Montana with this policy.

How can momondo help me find flights from Montana to Chicago?

Once you have performed a search for Montana to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Montana to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Montana to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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