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Cheap flights from Helena to Chicago from $404

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Helena to Chicago departing on 11/13. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Helena to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:45 am - 4:50 pm
HLN
-
MDW
10h 05m
2 stops
Delta Logo
1:00 pm - 10:41 pm
MDW
-
HLN
10h 41m
2 stops
$404Delta
Fri, Nov 13 - Sun, Nov 15
Delta Logo
5:45 am - 4:50 pm
HLN
-
MDW
10h 05m
2 stops
Delta Logo
1:00 pm - 10:41 pm
MDW
-
HLN
10h 41m
2 stops
$503Delta
Fri, Nov 13 - Sun, Nov 15
Delta Logo
5:45 am - 4:50 pm
HLN
-
MDW
10h 05m
2 stops
Delta Logo
1:00 pm - 10:41 pm
MDW
-
HLN
10h 41m
2 stops
$537Delta
Fri, Nov 13 - Sun, Nov 15
Delta Logo
5:40 am - 6:33 pm
HLN
-
MDW
11h 53m
2 stops
Delta Logo
1:25 pm - 10:30 pm
MDW
-
HLN
10h 05m
2 stops
$764Delta
Fri, Aug 14 - Mon, Aug 24
Delta Logo
5:40 am - 6:33 pm
HLN
-
MDW
11h 53m
2 stops
Delta Logo
1:25 pm - 10:30 pm
MDW
-
HLN
10h 05m
2 stops
$784Delta
Fri, Aug 14 - Mon, Aug 24
Delta Logo
5:40 am - 6:33 pm
HLN
-
MDW
11h 53m
2 stops
Delta Logo
1:25 pm - 10:30 pm
MDW
-
HLN
10h 05m
2 stops
$814Delta
Fri, Aug 14 - Mon, Aug 24
Delta Logo
5:40 am - 6:33 pm
HLN
-
MDW
11h 53m
2 stops
Delta Logo
10:54 am - 10:30 pm
MDW
-
HLN
12h 36m
2 stops
$857Delta
Mon, Aug 24 - Tue, Sep 1
Delta Logo
5:40 am - 6:33 pm
HLN
-
MDW
11h 53m
2 stops
Delta Logo
1:25 pm - 10:30 pm
MDW
-
HLN
10h 05m
2 stops
$922Delta
Fri, Aug 14 - Mon, Aug 24
Delta Logo
5:40 am - 6:25 pm
HLN
-
MDW
11h 45m
2 stops
Delta Logo
12:46 pm - 10:30 pm
MDW
-
HLN
10h 44m
2 stops
$1,198Delta
Wed, Jul 29 - Tue, Aug 4
Delta Logo
5:40 am - 6:25 pm
HLN
-
MDW
11h 45m
2 stops
Delta Logo
10:54 am - 10:30 pm
MDW
-
HLN
12h 36m
2 stops
$1,289Delta
Wed, Jul 29 - Tue, Aug 4

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Delta flights from Helena to Chicago Midway Airport

Our best Delta deals on Helena to Chicago Midway Airport flight tickets
Delta
Nov 13
HLN5:45 amHelena
10h 05m
2 stops
MDW4:50 pmChicago Midway
Nov 15
MDW1:00 pmChicago Midway
10h 41m
2 stops
HLN10:41 pmHelena
$404
Delta
Nov 13
HLN5:45 amHelena
10h 05m
2 stops
MDW4:50 pmChicago Midway
Nov 15
MDW1:00 pmChicago Midway
10h 41m
2 stops
HLN10:41 pmHelena
$503
Delta
Aug 14
HLN5:40 amHelena
11h 53m
2 stops
MDW6:33 pmChicago Midway
Aug 24
MDW1:25 pmChicago Midway
10h 05m
2 stops
HLN10:30 pmHelena
$764

momondo Fare Finder

 
Customize your flight search to find flights from Helena 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 June 27, 2026.
Use the filters below to find and compare flights from Helena to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 11/13

5:45 am-4:50 pm

2 stops10h 05m

Chicago Midway

Sun 11/15

1:00 pm-10:41 pm

2 stops10h 41m

$404

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 11/13

5:45 am-4:50 pm

2 stops10h 05m

Chicago Midway

Sun 11/15

1:00 pm-10:41 pm

2 stops10h 41m

$503

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 11/13

5:45 am-4:50 pm

2 stops10h 05m

Chicago Midway

Sun 11/15

1:00 pm-10:41 pm

2 stops10h 41m

$537

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Mon 8/24

1:25 pm-10:30 pm

2 stops10h 05m

$764

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Mon 8/24

1:25 pm-10:30 pm

2 stops10h 05m

$784

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Mon 8/24

1:25 pm-10:30 pm

2 stops10h 05m

$814

HelenaChicago

HLN - MDW

HLNMDW

Helena

Mon 8/24

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Tue 9/1

10:54 am-10:30 pm

2 stops12h 36m

$857

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 8/14

5:40 am-6:33 pm

2 stops11h 53m

Chicago Midway

Mon 8/24

1:25 pm-10:30 pm

2 stops10h 05m

$922

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 7/29

5:40 am-6:25 pm

2 stops11h 45m

Chicago Midway

Tue 8/4

12:46 pm-10:30 pm

2 stops10h 44m

$1,198

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 7/29

5:40 am-6:25 pm

2 stops11h 45m

Chicago Midway

Tue 8/4

10:54 am-10:30 pm

2 stops12h 36m

$1,289

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Helena 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 Helena to Chicago Midway?

Delta is the most popular carrier operating from Helena to Chicago Midway

When to book flights from Helena to Chicago Midway Airport

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

Cheap Helena to Chicago Midway Airport (HLN to MDW) flight deals and tips

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

Fastest flight time

9h 35m

Direct flights

None
The fastest flight from Helena to Chicago Midway Airport takes 9h 35m
There are no direct flights from Helena to Chicago Midway Airport. There are no popular flight routes from Helena to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Helena to Chicago Midway Airport

  • How far is Helena to Chicago Midway by plane?

    Chicago Midway is 1242.0 mi away from Helena. By plane, this route typically takes 9h 35m.

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

    Prices for flights from Helena Airport to Chicago Midway Airport are updated daily.

  • How old do you have to be to fly from Helena 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 Helena 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
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New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Helena to Chicago for you.

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

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

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

Once you have performed a search for Helena 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 Helena to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Helena. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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