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Cheap flights from Billings to Chicago from $186

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Billings to Chicago departing on 9/20. 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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0 bags

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Find the cheapest flights from Billings to Chicago

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
$229Delta
Find Deal
Wed, Oct 22 - Sat, Oct 25
Delta Logo
6:25 am - 1:08 pmBIL-MDW
5h 43m1 stop
Delta Logo
3:00 pm - 11:05 pmMDW-BIL
9h 05m2 stops
$234Delta
Find Deal
Wed, Oct 22 - Sat, Oct 25
Delta Logo
5:18 am - 6:08 pmBIL-MDW
11h 50m2 stops
Delta Logo
6:00 am - 5:44 pmMDW-BIL
12h 44m2 stops
$239Delta
Find Deal
Wed, Nov 12 - Sat, Nov 15
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
Wed, Oct 22 - Sat, Oct 25
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
Wed, Oct 22 - Sat, Oct 25
Delta Logo
6:25 am - 6:25 pmBIL-MDW
11h 00m2 stops
Delta Logo
3:00 pm - 11:05 pmMDW-BIL
9h 05m2 stops
$259Delta
Find Deal
Wed, Oct 22 - Sat, Oct 25
Delta Logo
6:25 am - 6:25 pmBIL-MDW
11h 00m2 stops
Delta Logo
3:00 pm - 11:05 pmMDW-BIL
9h 05m2 stops
$354Delta
Find Deal
Wed, Oct 22 - Sat, Oct 25
Delta Logo
6:25 am - 1:03 pmBIL-MDW
5h 38m1 stop
Delta Logo
7:15 pm - 11:10 pmMDW-BIL
4h 55m1 stop
$380Delta
Find Deal
Tue, Sep 23 - Fri, Sep 26
Delta Logo
6:25 am - 1:03 pmBIL-MDW
5h 38m1 stop
Delta Logo
7:10 pm - 11:18 pmMDW-BIL
5h 08m1 stop
$420Delta
Find Deal
Sun, Oct 5 - Tue, Oct 7
Delta Logo
6:25 am - 1:03 pmBIL-MDW
5h 38m1 stop
Delta Logo
7:15 pm - 11:10 pmMDW-BIL
4h 55m1 stop
$424Delta
Find Deal
Wed, Sep 10 - Sun, Sep 14

Delta flights from Billings to Chicago Midway Airport

Our best Delta deals on Billings to Chicago Midway Airport flight tickets
Delta
Oct 22
BIL6:25 amBillings Logan Intl
5h 43m
1 stop
MDW1:08 pmChicago Midway
Oct 25
MDW3:00 pmChicago Midway
5h 42m
1 stop
BIL7:42 pmBillings Logan Intl
$229
Find similar
Delta
Oct 22
BIL6:25 amBillings Logan Intl
5h 43m
1 stop
MDW1:08 pmChicago Midway
Oct 25
MDW3:00 pmChicago Midway
9h 05m
2 stops
BIL11:05 pmBillings Logan Intl
$234
Find similar
Delta
Nov 12
BIL5:18 amBillings Logan Intl
11h 50m
2 stops
MDW6:08 pmChicago Midway
Nov 15
MDW6:00 amChicago Midway
12h 44m
2 stops
BIL5:44 pmBillings Logan Intl
$239
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Billings 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 August 28, 2025.
Use the filters below to find and compare flights from Billings to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Wed 10/22

6:25 am-1:08 pm

1 stop5h 43m

Chicago Midway

Sat 10/25

3:00 pm-7:42 pm

1 stop5h 42m

$229

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Wed 10/22

6:25 am-1:08 pm

1 stop5h 43m

Chicago Midway

Sat 10/25

3:00 pm-11:05 pm

2 stops9h 05m

$234

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Wed 11/12

5:18 am-6:08 pm

2 stops11h 50m

Chicago Midway

Sat 11/15

6:00 am-5:44 pm

2 stops12h 44m

$239

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Wed 10/22

6:25 am-1:08 pm

1 stop5h 43m

Chicago Midway

Sat 10/25

3:00 pm-7:42 pm

1 stop5h 42m

$249

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Wed 10/22

6:25 am-1:08 pm

1 stop5h 43m

Chicago Midway

Sat 10/25

3:00 pm-11:05 pm

2 stops9h 05m

$254

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Wed 10/22

6:25 am-6:25 pm

2 stops11h 00m

Chicago Midway

Sat 10/25

3:00 pm-11:05 pm

2 stops9h 05m

$259

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Wed 10/22

6:25 am-6:25 pm

2 stops11h 00m

Chicago Midway

Sat 10/25

3:00 pm-11:05 pm

2 stops9h 05m

$354

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Tue 9/23

6:25 am-1:03 pm

1 stop5h 38m

Chicago Midway

Fri 9/26

7:15 pm-11:10 pm

1 stop4h 55m

$380

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Sun 10/5

6:25 am-1:03 pm

1 stop5h 38m

Chicago Midway

Tue 10/7

7:10 pm-11:18 pm

1 stop5h 08m

$420

BillingsChicago

BIL - MDW

BILMDW

Billings Logan Intl

Wed 9/10

6:25 am-1:03 pm

1 stop5h 38m

Chicago Midway

Sun 9/14

7:15 pm-11:10 pm

1 stop4h 55m

$424

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 Billings 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 airline that flies from Billings Logan Intl to Chicago Midway?

Delta is the most popular carrier operating from Billings Logan Intl to Chicago Midway

When to book flights from Billings to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Billings to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Billings to Chicago Midway Airport (BIL to MDW) flight deals and tips

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

Direct flights

None
There are no direct flights from Billings to Chicago Midway Airport. There are no popular flight routes from Billings to Chicago Midway Airport.
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  • How far is Billings Logan Intl to Chicago Midway by plane?

    The straight-line distance from Billings Logan Intl to Chicago Midway is 1067.3 mi. By plane, this route typically takes 5h 38m.

  • When did momondo last update prices for flights from Billings Logan Intl Airport to Chicago Midway Airport?

    Prices for flights from Billings Logan Intl Airport to Chicago Midway Airport are updated daily.

  • How old do you have to be to fly from Billings Logan Intl Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Billings Logan Intl Airport to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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 Billings to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Billings.

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

momondo does allow users to show only those flights to Chicago from Billings which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Billings to Chicago.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Billings and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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