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Cheap flights from Montana to Chicago from $135

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 11/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Delta Logo
6:25 am - 1:08 pmBIL-MDW
5h 43m1 stop
Delta Logo
3:00 pm - 7:42 pmMDW-BIL
5h 42m1 stop
$249Delta
Find Deal
Sat, Nov 1 - Sat, Nov 8
Delta Logo
6:25 am - 1:08 pmBIL-MDW
5h 43m1 stop
Delta Logo
3:00 pm - 11:05 pmMDW-BIL
9h 05m2 stops
$254Delta
Find Deal
Sat, Nov 1 - Sat, Nov 8
Delta Logo
2:29 pm - 10:14 pmBZN-MDW
6h 45m1 stop
Delta Logo
6:00 am - 1:19 pmMDW-BZN
8h 19m1 stop
$269Delta
Find Deal
Tue, Oct 21 - Thu, Oct 23
Delta Logo
6:15 am - 6:34 pmBIL-MDW
11h 19m2 stops
Delta Logo
6:45 pm - 10:50 pmMDW-BIL
5h 05m1 stop
$269Delta
Find Deal
Thu, Feb 26 - Mon, Mar 2
Delta Logo
6:00 am - 1:08 pmBZN-MDW
6h 08m1 stop
Delta Logo
6:00 am - 5:39 pmMDW-BZN
12h 39m2 stops
$274Delta
Find Deal
Sat, Nov 1 - Tue, Nov 4
Delta Logo
2:29 pm - 10:14 pmBZN-MDW
6h 45m1 stop
Delta Logo
7:10 pm - 11:37 pmMDW-BZN
5h 27m1 stop
$280Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Southwest Logo
8:00 pm - 5:15 amBZN-MDW
8h 15m1 stop
Southwest Logo
10:45 pm - 9:50 amMDW-BZN
12h 05m1 stop
$285Southwest
Find Deal
Thu, Oct 23 - Sun, Oct 26
Delta Logo
5:20 am - 5:43 pmFCA-MDW
11h 23m2 stops
Delta Logo
9:20 am - 2:29 pmMDW-FCA
6h 09m1 stop
$294Delta
Find Deal
Sat, Oct 25 - Sat, Nov 1
Delta Logo
6:25 am - 1:08 pmBIL-MDW
5h 43m1 stop
Delta Logo
1:08 pm - 10:25 pmMDW-BIL
10h 17m2 stops
$299Delta
Find Deal
Sat, Oct 25 - Wed, Oct 29
Southwest Logo
5:00 am - 2:25 pmBZN-MDW
8h 25m2 stops
Southwest Logo
5:15 am - 9:35 amMDW-BZN
5h 20m1 stop
$345Southwest
Find Deal
Thu, Oct 30 - Sun, Nov 2

Delta flights from Montana to Chicago Midway Airport

Our best Delta deals on Montana to Chicago Midway Airport flight tickets
Delta
Nov 1
BIL6:25 amBillings Logan Intl
5h 43m
1 stop
MDW1:08 pmChicago Midway
Nov 8
MDW3:00 pmChicago Midway
5h 42m
1 stop
BIL7:42 pmBillings Logan Intl
$249
Find similar
Delta
Nov 1
BIL6:25 amBillings Logan Intl
5h 43m
1 stop
MDW1:08 pmChicago Midway
Nov 8
MDW3:00 pmChicago Midway
9h 05m
2 stops
BIL11:05 pmBillings Logan Intl
$254
Find similar
Delta
Feb 26
BIL6:15 amBillings Logan Intl
11h 19m
2 stops
MDW6:34 pmChicago Midway
Mar 2
MDW6:45 pmChicago Midway
5h 05m
1 stop
BIL10:50 pmBillings Logan Intl
$269
Find similar

Southwest flights from Montana to Chicago Midway Airport

Our best Southwest deals on Montana to Chicago Midway Airport flight tickets
Southwest
Oct 23
BZN8:00 pmBozeman Gallatin Field
8h 15m
1 stop
MDW5:15 amChicago Midway
Oct 26
MDW10:45 pmChicago Midway
12h 05m
1 stop
BZN9:50 amBozeman Gallatin Field
$285
Find similar
Southwest
Oct 30
BZN5:00 amBozeman Gallatin Field
8h 25m
2 stops
MDW2:25 pmChicago Midway
Nov 2
MDW5:15 amChicago Midway
5h 20m
1 stop
BZN9:35 amBozeman Gallatin Field
$345
Find similar
Southwest
Oct 23
BZN6:00 amBozeman Gallatin Field
8h 55m
2 stops
MDW3:55 pmChicago Midway
Oct 26
MDW6:35 pmChicago Midway
6h 50m
2 stops
BZN12:25 amBozeman Gallatin Field
$350
Find similar

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 September 18, 2025.
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

Sat 11/1

6:25 am-1:08 pm

1 stop5h 43m

Chicago Midway

Sat 11/8

3:00 pm-7:42 pm

1 stop5h 42m

$249

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sat 11/1

6:25 am-1:08 pm

1 stop5h 43m

Chicago Midway

Sat 11/8

3:00 pm-11:05 pm

2 stops9h 05m

$254

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Tue 10/21

2:29 pm-10:14 pm

1 stop6h 45m

Chicago Midway

Thu 10/23

6:00 am-1:19 pm

1 stop8h 19m

$269

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Thu 2/26

6:15 am-6:34 pm

2 stops11h 19m

Chicago Midway

Mon 3/2

6:45 pm-10:50 pm

1 stop5h 05m

$269

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Sat 11/1

6:00 am-1:08 pm

1 stop6h 08m

Chicago Midway

Tue 11/4

6:00 am-5:39 pm

2 stops12h 39m

$274

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Thu 10/23

2:29 pm-10:14 pm

1 stop6h 45m

Chicago Midway

Mon 10/27

7:10 pm-11:37 pm

1 stop5h 27m

$280

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Thu 10/23

8:00 pm-5:15 am

1 stop8h 15m

Chicago Midway

Sun 10/26

10:45 pm-9:50 am

1 stop12h 05m

$285

KalispellChicago

FCA - MDW

FCAMDW

Kalispell Glacier Park

Sat 10/25

5:20 am-5:43 pm

2 stops11h 23m

Chicago Midway

Sat 11/1

9:20 am-2:29 pm

1 stop6h 09m

$294

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sat 10/25

6:25 am-1:08 pm

1 stop5h 43m

Chicago Midway

Wed 10/29

1:08 pm-10:25 pm

2 stops10h 17m

$299

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Thu 10/30

5:00 am-2:25 pm

2 stops8h 25m

Chicago Midway

Sun 11/2

5:15 am-9:35 am

1 stop5h 20m

$345

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, Friday is the cheapest day to fly to Chicago Midway Airport from Montana. The lowest ticket price found for a Friday departure recently was $348. 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 $596.

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?

No. A direct flight is the cheapest option for a flight between Montana to Chicago Midway Airport.

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

Best Price Found

$210

Fastest flight time

2h 55m

Direct flights

Sat
The best one-way flight to Chicago Midway Airport from Montana in the past 72 hours is $210. The best round-trip flight deal from Montana to Chicago Midway Airport found on momondo in the last 72 hours is $290.
The fastest flight from Montana to Chicago Midway Airport takes 2h 55m
Direct flights go from Montana to Chicago Midway Airport on Saturday. The only airline offering direct flights is Southwest.
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 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?

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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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