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Cheap flights from Helena to Chicago from $235

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Helena to Chicago departing on 5/6. 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 Helena to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:30 am - 5:37 pm
HLN
-
MDW
11h 07m
2 stops
Delta Logo
10:49 am - 10:27 pm
MDW
-
HLN
12h 38m
2 stops
$709Delta
Fri, Feb 20 - Tue, Feb 24
Delta Logo
5:30 am - 5:45 pm
HLN
-
MDW
11h 15m
2 stops
Delta Logo
1:29 pm - 10:27 pm
MDW
-
HLN
9h 58m
2 stops
$979Delta
Wed, Mar 4 - Fri, Mar 6

Delta flights from Helena to Chicago Midway Airport

Our best Delta deals on Helena to Chicago Midway Airport flight tickets
Delta
Feb 20
HLN5:30 amHelena
11h 07m
2 stops
MDW5:37 pmChicago Midway
Feb 24
MDW10:49 amChicago Midway
12h 38m
2 stops
HLN10:27 pmHelena
$709
Delta
Mar 4
HLN5:30 amHelena
11h 15m
2 stops
MDW5:45 pmChicago Midway
Mar 6
MDW1:29 pmChicago Midway
9h 58m
2 stops
HLN10:27 pmHelena
$979

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 February 6, 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

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 2/20

5:30 am-5:37 pm

2 stops11h 07m

Chicago Midway

Tue 2/24

10:49 am-10:27 pm

2 stops12h 38m

$709

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 3/4

5:30 am-5:45 pm

2 stops11h 15m

Chicago Midway

Fri 3/6

1:29 pm-10:27 pm

2 stops9h 58m

$979

HelenaChicago

HLN - MDW

HLNMDW

Helena

Wed 5/6

5:40 am-5:58 pm

2 stops11h 18m

$235

HelenaChicago

HLN - MDW

HLNMDW

Helena

Fri 5/8

5:45 am-9:09 pm

2 stops14h 24m

$265

HelenaChicago

HLN - MDW

HLNMDW

Helena

Tue 5/5

1:04 pm-9:56 am

2 stops19h 52m

$369

HelenaChicago

HLN - MDW

HLNMDW

Helena

Mon 5/11

1:00 pm-12:42 pm

2 stops22h 42m

$393

HelenaChicago

HLN - MDW

HLNMDW

Helena

Thu 5/7

1:00 pm-11:56 am

2 stops21h 56m

$416

HelenaChicago

HLN - MDW

HLNMDW

Helena

Sun 5/10

1:00 pm-12:42 pm

2 stops22h 42m

$438

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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

11h 07m

Direct flights

None
The fastest flight from Helena to Chicago Midway Airport takes 11h 07m
There are no direct flights from Helena to Chicago Midway Airport. There are no popular flight routes from Helena to Chicago Midway Airport.
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  • How far is Helena to Chicago Midway by plane?

    Chicago Midway is 1242.0 mi away from Helena. By plane, this route typically takes 11h 07m.

  • 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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Munster
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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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