Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Montana to Chicago from $143

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 6/24. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Montana to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:24 am - 1:09 pm
BIL
-
MDW
5h 45m
1 stop
Delta Logo
7:06 pm - 11:30 pm
MDW
-
BIL
5h 24m
1 stop
$271Delta
Sat, Jul 18 - Tue, Jul 21
Delta Logo
6:34 pm - 9:08 am
BIL
-
MDW
13h 34m
2 stops
Delta Logo
1:49 pm - 7:59 pm
MDW
-
BIL
7h 10m
1 stop
$276Delta
Tue, Jul 14 - Sat, Jul 25
Southwest Logo
12:55 pm - 4:50 pm
BZN
-
MDW
2h 55mnonstop
Southwest Logo
10:20 am - 12:30 pm
MDW
-
BZN
3h 10mnonstop
$285Southwest
Wed, Aug 26 - Sun, Aug 30
Southwest Logo
2:30 pm - 11:45 pm
BZN
-
MDW
8h 15m
1 stop
Southwest Logo
10:50 am - 12:55 pm
MDW
-
BZN
3h 05mnonstop
$295Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
2:00 pm - 10:20 pm
BZN
-
MDW
7h 20m
2 stops
Southwest Logo
10:20 am - 12:30 pm
MDW
-
BZN
3h 10mnonstop
$300Southwest
Wed, Aug 26 - Sun, Aug 30
Southwest Logo
7:35 am - 11:25 am
BZN
-
MDW
2h 50mnonstop
Southwest Logo
6:10 am - 7:40 pm
MDW
-
BZN
14h 30m
1 stop
$301Southwest
Thu, Jul 2 - Sun, Jul 5
Delta Logo
6:00 am - 1:09 pm
BZN
-
MDW
6h 09m
1 stop
Delta Logo
1:49 pm - 7:44 pm
MDW
-
BZN
6h 55m
1 stop
$305Delta
Tue, Jul 7 - Sat, Jul 18
Delta Logo
6:24 am - 1:09 pm
BIL
-
MDW
5h 45m
1 stop
Delta Logo
1:18 pm - 11:30 pm
MDW
-
BIL
11h 12m
2 stops
$307Delta
Sat, Jul 18 - Tue, Jul 21
Delta Logo
6:00 am - 1:09 pm
BZN
-
MDW
6h 09m
1 stop
Delta Logo
1:18 pm - 11:52 pm
MDW
-
BZN
11h 34m
2 stops
$310Delta
Tue, Jul 7 - Tue, Jul 14
Delta Logo
6:34 pm - 9:08 am
BIL
-
MDW
13h 34m
2 stops
Delta Logo
1:18 pm - 11:30 pm
MDW
-
BIL
11h 12m
2 stops
$312Delta
Tue, Jul 14 - Tue, Jul 21

Delta flights from Montana to Chicago Midway Airport

Our best Delta deals on Montana to Chicago Midway Airport flight tickets
Delta
Jul 18
BIL6:24 amBillings Logan Intl
5h 45m
1 stop
MDW1:09 pmChicago Midway
Jul 21
MDW7:06 pmChicago Midway
5h 24m
1 stop
BIL11:30 pmBillings Logan Intl
$271
Delta
Jul 14
BIL6:34 pmBillings Logan Intl
13h 34m
2 stops
MDW9:08 amChicago Midway
Jul 25
MDW1:49 pmChicago Midway
7h 10m
1 stop
BIL7:59 pmBillings Logan Intl
$276
Delta
Jul 7
BZN6:00 amBozeman Gallatin Field
6h 09m
1 stop
MDW1:09 pmChicago Midway
Jul 18
MDW1:49 pmChicago Midway
6h 55m
1 stop
BZN7:44 pmBozeman Gallatin Field
$305

Southwest flights from Montana to Chicago Midway Airport

Our best Southwest deals on Montana to Chicago Midway Airport flight tickets
Southwest
Aug 26
BZN12:55 pmBozeman Gallatin Field
2h 55m
MDW4:50 pmChicago Midway
Aug 30
MDW10:20 amChicago Midway
3h 10m
BZN12:30 pmBozeman Gallatin Field
$285
Southwest
Aug 13
BZN2:30 pmBozeman Gallatin Field
8h 15m
1 stop
MDW11:45 pmChicago Midway
Aug 17
MDW10:50 amChicago Midway
3h 05m
BZN12:55 pmBozeman Gallatin Field
$295
Southwest
Aug 26
BZN2:00 pmBozeman Gallatin Field
7h 20m
2 stops
MDW10:20 pmChicago Midway
Aug 30
MDW10:20 amChicago Midway
3h 10m
BZN12:30 pmBozeman Gallatin Field
$300

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 May 27, 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

Cheapest round-trip

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sat 7/18

6:24 am-1:09 pm

1 stop5h 45m

Chicago Midway

Tue 7/21

7:06 pm-11:30 pm

1 stop5h 24m

$271

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Tue 7/14

6:34 pm-9:08 am

2 stops13h 34m

Chicago Midway

Sat 7/25

1:49 pm-7:59 pm

1 stop7h 10m

$276
Quickest round-trip

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Wed 8/26

12:55 pm-4:50 pm

Nonstop2h 55m

Chicago Midway

Sun 8/30

10:20 am-12:30 pm

Nonstop3h 10m

$285

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Thu 8/13

2:30 pm-11:45 pm

1 stop8h 15m

Chicago Midway

Mon 8/17

10:50 am-12:55 pm

Nonstop3h 05m

$295

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Wed 8/26

2:00 pm-10:20 pm

2 stops7h 20m

Chicago Midway

Sun 8/30

10:20 am-12:30 pm

Nonstop3h 10m

$300

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Thu 7/2

7:35 am-11:25 am

Nonstop2h 50m

Chicago Midway

Sun 7/5

6:10 am-7:40 pm

1 stop14h 30m

$301

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Tue 7/7

6:00 am-1:09 pm

1 stop6h 09m

Chicago Midway

Sat 7/18

1:49 pm-7:44 pm

1 stop6h 55m

$305

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sat 7/18

6:24 am-1:09 pm

1 stop5h 45m

Chicago Midway

Tue 7/21

1:18 pm-11:30 pm

2 stops11h 12m

$307

BozemanChicago

BZN - MDW

BZNMDW

Bozeman Gallatin Field

Tue 7/7

6:00 am-1:09 pm

1 stop6h 09m

Chicago Midway

Tue 7/14

1:18 pm-11:52 pm

2 stops11h 34m

$310

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Tue 7/14

6:34 pm-9:08 am

2 stops13h 34m

Chicago Midway

Tue 7/21

1:18 pm-11:30 pm

2 stops11h 12m

$312

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Montana. The lowest ticket price found for a Wednesday departure recently was $443. 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, Friday 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 $571.

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 Airport flights?

There is only 1 cabin class available to choose from on Montana to Chicago Midway Airport 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

$209

Fastest flight time

2h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Montana in the past 72 hours is $209. The best round-trip flight deal from Montana to Chicago Midway Airport found on momondo in the last 72 hours is $416.
The fastest flight from Montana to Chicago Midway Airport takes 2h 50m
Direct flights go from Montana to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Montana to Chicago Midway Airport

  • 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
8,423 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 6/26
Fri 7/3
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago