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Cheap flights from Helena to Chicago from $296

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 8/14. 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 Helena to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
1:03 pm - 9:50 pm
HLN
-
ORD
7h 47m
1 stop
Delta Logo
7:45 am - 12:20 pm
ORD
-
HLN
5h 35m
1 stop
$329Delta
Fri, Jun 5 - Tue, Jun 9
Delta Logo
5:45 am - 11:52 am
HLN
-
ORD
5h 07m
1 stop
Delta Logo
7:45 am - 12:20 pm
ORD
-
HLN
5h 35m
1 stop
$354Delta
Tue, Jun 2 - Thu, Jul 2
Delta Logo
5:45 am - 11:52 am
HLN
-
ORD
5h 07m
1 stop
Delta Logo
7:45 am - 12:20 pm
ORD
-
HLN
5h 35m
1 stop
$364Delta
Tue, Jun 2 - Thu, Jul 2
United Airlines Logo
2:20 pm - 10:49 pm
HLN
-
ORD
7h 29m
1 stop
United Airlines Logo
7:05 am - 1:33 pm
ORD
-
HLN
7h 28m
1 stop
$389United Airlines
Sat, Jun 6 - Sat, Jun 13
Delta Logo
5:45 am - 11:52 am
HLN
-
ORD
5h 07m
1 stop
Delta Logo
7:45 am - 12:20 pm
ORD
-
HLN
5h 35m
1 stop
$399Delta
Tue, Jun 2 - Thu, Jul 2
United Airlines Logo
2:30 pm - 10:44 pm
HLN
-
ORD
7h 14m
1 stop
United Airlines Logo
8:55 am - 1:27 pm
ORD
-
HLN
5h 32m
1 stop
$419United Airlines
Tue, Oct 27 - Sat, Oct 31
Delta Logo
5:45 am - 6:41 pm
HLN
-
ORD
11h 56m
2 stops
Delta Logo
7:45 am - 12:20 pm
ORD
-
HLN
5h 35m
1 stop
$454Delta
Tue, Jun 2 - Thu, Jul 2
Delta Logo
5:45 am - 6:41 pm
HLN
-
ORD
11h 56m
2 stops
Delta Logo
7:45 am - 12:20 pm
ORD
-
HLN
5h 35m
1 stop
$459Delta
Tue, Jun 2 - Thu, Jul 2
United Airlines Logo
2:29 pm - 11:59 pm
HLN
-
ORD
8h 30m
1 stop
United Airlines Logo
6:00 am - 1:32 pm
ORD
-
HLN
8h 32m
1 stop
$479United Airlines
Wed, Sep 2 - Sat, Sep 5
Delta Logo
5:45 am - 4:29 pm
HLN
-
ORD
9h 44m
2 stops
Delta Logo
7:45 am - 12:20 pm
ORD
-
HLN
5h 35m
1 stop
$494Delta
Tue, Jun 2 - Thu, Jul 2

United Airlines flights from Helena to Chicago

Our best United Airlines deals on Helena to Chicago flight tickets
United Airlines
Jun 6
HLN2:20 pmHelena
7h 29m
1 stop
ORD10:49 pmChicago O'Hare Intl
Jun 13
ORD7:05 amChicago O'Hare Intl
7h 28m
1 stop
HLN1:33 pmHelena
$389
United Airlines
Oct 27
HLN2:30 pmHelena
7h 14m
1 stop
ORD10:44 pmChicago O'Hare Intl
Oct 31
ORD8:55 amChicago O'Hare Intl
5h 32m
1 stop
HLN1:27 pmHelena
$419
United Airlines
Sep 2
HLN2:29 pmHelena
8h 30m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 5
ORD6:00 amChicago O'Hare Intl
8h 32m
1 stop
HLN1:32 pmHelena
$479

Alaska Airlines flights from Helena to Chicago

Our best Alaska Airlines deals on Helena to Chicago flight tickets
Alaska Airlines
Jun 6
HLN4:43 pmHelena
26h 16m
2 stops
ORD7:59 pmChicago O'Hare Intl
Jun 13
ORD6:00 amChicago O'Hare Intl
11h 32m
1 stop
HLN4:32 pmHelena
$495
Alaska Airlines
Sep 2
HLN5:11 pmHelena
12h 11m
1 stop
ORD6:22 amChicago O'Hare Intl
Sep 5
ORD9:00 amChicago O'Hare Intl
8h 34m
1 stop
HLN4:34 pmHelena
$515
Alaska Airlines
May 22
HLN4:43 pmHelena
12h 37m
1 stop
ORD6:20 amChicago O'Hare Intl
May 26
ORD7:49 pmChicago O'Hare Intl
21h 17m
1 stop
HLN4:06 pmHelena
$669

momondo Fare Finder

 
Customize your flight search to find flights from Helena to Chicago 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 9, 2026.
Use the filters below to find and compare flights from Helena to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 6/5

1:03 pm-9:50 pm

1 stop7h 47m

Chicago O'Hare Intl

Tue 6/9

7:45 am-12:20 pm

1 stop5h 35m

$329
Quickest round-trip

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 6/2

5:45 am-11:52 am

1 stop5h 07m

Chicago O'Hare Intl

Thu 7/2

7:45 am-12:20 pm

1 stop5h 35m

$354

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 6/2

5:45 am-11:52 am

1 stop5h 07m

Chicago O'Hare Intl

Thu 7/2

7:45 am-12:20 pm

1 stop5h 35m

$364

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 6/6

2:20 pm-10:49 pm

1 stop7h 29m

Chicago O'Hare Intl

Sat 6/13

7:05 am-1:33 pm

1 stop7h 28m

$389

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 6/2

5:45 am-11:52 am

1 stop5h 07m

Chicago O'Hare Intl

Thu 7/2

7:45 am-12:20 pm

1 stop5h 35m

$399

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 10/27

2:30 pm-10:44 pm

1 stop7h 14m

Chicago O'Hare Intl

Sat 10/31

8:55 am-1:27 pm

1 stop5h 32m

$419

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 6/2

5:45 am-6:41 pm

2 stops11h 56m

Chicago O'Hare Intl

Thu 7/2

7:45 am-12:20 pm

1 stop5h 35m

$454

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 6/2

5:45 am-6:41 pm

2 stops11h 56m

Chicago O'Hare Intl

Thu 7/2

7:45 am-12:20 pm

1 stop5h 35m

$459

HelenaChicago

HLN - ORD

HLNORD

Helena

Wed 9/2

2:29 pm-11:59 pm

1 stop8h 30m

Chicago O'Hare Intl

Sat 9/5

6:00 am-1:32 pm

1 stop8h 32m

$479

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 6/2

5:45 am-4:29 pm

2 stops9h 44m

Chicago O'Hare Intl

Thu 7/2

7:45 am-12:20 pm

1 stop5h 35m

$494

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 Helena to Chicago

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?

Alaska Airlines, Delta, and United Airlines are the most popular carriers operating from Helena to Chicago

What airlines fly to Chicago?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Helena according to our data. United Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When to book flights from Helena to Chicago

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

Cheap Helena to Chicago (HLN to CHI) flight deals and tips

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

Fastest flight time

5h 25m

Direct flights

None
The fastest flight from Helena to Chicago takes 5h 25m
There are no direct flights from Helena to Chicago. There are no popular flight routes from Helena to Chicago.
Search flight deals

Frequently asked questions about flying from Helena to Chicago

  • How far is Helena to Chicago by plane?

    There are 1245.1 mi between Helena and Chicago. 5h 25m is a normal flight duration for this route.

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

    Prices for flights from Helena Airport to Chicago are refreshed on a daily basis.

  • How old do you have to be to fly from Helena Airport to Chicago?

    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 Helena Airport to Chicago.

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

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Helena to Chicago?

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 Helena to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Helena to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Helena to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

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

Price alerts on flights to Chicago from Helena are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport