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Cheap flights from Helena to Chicago from $250

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 10/22. 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.
United Airlines Logo
2:26 pm - 10:00 pmHLN  Helena-ORD Chicago O'Hare Intl
6h 34m1 stop Denver Intl
United Airlines Logo
7:00 am - 1:45 pmORD  Chicago O'Hare Intl-HLN Helena
7h 45m1 stop Denver Intl
$339United Airlines
Wed, Sep 16 - Sat, Sep 19
Delta Logo
1:04 pm - 11:59 pmHLN  Helena-ORD Chicago O'Hare Intl
9h 55m2 stops Salt Lake City Atlanta Hartsfield-Jackson
Delta Logo
7:35 am - 12:22 pmORD  Chicago O'Hare Intl-HLN Helena
5h 47m1 stop Salt Lake City
$344Delta
Wed, Nov 18 - Mon, Nov 23
Delta Logo
1:08 pm - 10:00 pmHLN  Helena-ORD Chicago O'Hare Intl
7h 52m1 stop Salt Lake City
Delta Logo
7:35 am - 12:28 pmORD  Chicago O'Hare Intl-HLN Helena
5h 53m1 stop Salt Lake City
$369Delta
Fri, Nov 6 - Sun, Nov 8
Delta Logo
1:08 pm - 11:52 pmHLN  Helena-ORD Chicago O'Hare Intl
9h 44m2 stops Salt Lake City Atlanta Hartsfield-Jackson
Delta Logo
7:35 am - 12:28 pmORD  Chicago O'Hare Intl-HLN Helena
5h 53m1 stop Salt Lake City
$374Delta
Fri, Nov 6 - Sun, Nov 8
United Airlines Logo
2:30 pm - 10:46 pmHLN  Helena-ORD Chicago O'Hare Intl
7h 16m1 stop Denver Intl
United Airlines Logo
7:00 am - 1:48 pmORD  Chicago O'Hare Intl-HLN Helena
7h 48m1 stop Denver Intl
$396United Airlines
Wed, Oct 14 - Sat, Oct 17
United Airlines Logo
2:35 pm - 10:46 pmHLN  Helena-ORD Chicago O'Hare Intl
7h 11m1 stop Denver Intl
United Airlines Logo
2:42 pm - 9:30 pmORD  Chicago O'Hare Intl-HLN Helena
7h 48m1 stop Denver Intl
$409United Airlines
Tue, Aug 25 - Sat, Aug 29
Delta Logo
12:55 pm - 9:33 pmHLN  Helena-ORD Chicago O'Hare Intl
7h 38m1 stop Salt Lake City
Delta Logo
6:00 am - 12:15 pmORD  Chicago O'Hare Intl-HLN Helena
7h 15m2 stops Minneapolis St Paul Salt Lake City
$414Delta
Tue, Aug 25 - Sat, Aug 29
Alaska Airlines Logo
5:18 pm - 7:21 pmHLN  Helena-ORD Chicago O'Hare Intl
25h 03m2 stops Seattle/Tacoma Intl San Diego
Alaska Airlines Logo
6:00 am - 4:41 pmORD  Chicago O'Hare Intl-HLN Helena
11h 41m1 stop Seattle/Tacoma Intl
$462Alaska Airlines
Fri, Sep 25 - Mon, Sep 28
Alaska Airlines Logo
5:18 pm - 6:20 amHLN  Helena-ORD Chicago O'Hare Intl
12h 02m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
6:00 am - 4:41 pmORD  Chicago O'Hare Intl-HLN Helena
11h 41m1 stop Seattle/Tacoma Intl
$469Alaska Airlines
Fri, Sep 25 - Sun, Sep 27
Alaska Airlines Logo
5:26 pm - 5:40 amHLN  Helena-ORD Chicago O'Hare Intl
11h 14m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
7:16 pm - 4:49 pmORD  Chicago O'Hare Intl-HLN Helena
22h 33m1 stop Seattle/Tacoma Intl
$489Alaska Airlines
Thu, Oct 15 - Mon, Oct 19

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United Airlines flights from Helena to Chicago

Our best United Airlines deals on Helena to Chicago flight tickets
United Airlines
Sep 16
HLN2:26 pmHelena
6h 34m
1 stop
ORD10:00 pmChicago O'Hare Intl
Sep 19
ORD7:00 amChicago O'Hare Intl
7h 45m
1 stop
HLN1:45 pmHelena
$339
United Airlines
Oct 14
HLN2:30 pmHelena
7h 16m
1 stop
ORD10:46 pmChicago O'Hare Intl
Oct 17
ORD7:00 amChicago O'Hare Intl
7h 48m
1 stop
HLN1:48 pmHelena
$396
United Airlines
Aug 25
HLN2:35 pmHelena
7h 11m
1 stop
ORD10:46 pmChicago O'Hare Intl
Aug 29
ORD2:42 pmChicago O'Hare Intl
7h 48m
1 stop
HLN9:30 pmHelena
$409

Alaska Airlines flights from Helena to Chicago

Our best Alaska Airlines deals on Helena to Chicago flight tickets
Alaska Airlines
Sep 25
HLN5:18 pmHelena
12h 02m
1 stop
ORD6:20 amChicago O'Hare Intl
Sep 27
ORD6:00 amChicago O'Hare Intl
11h 41m
1 stop
HLN4:41 pmHelena
$469
Alaska Airlines
Oct 15
HLN5:26 pmHelena
11h 14m
1 stop
ORD5:40 amChicago O'Hare Intl
Oct 19
ORD7:16 pmChicago O'Hare Intl
22h 33m
1 stop
HLN4:49 pmHelena
$489
Alaska Airlines
Sep 25
HLN5:18 pmHelena
12h 02m
1 stop
ORD6:20 amChicago O'Hare Intl
Sep 26
ORD2:22 pmChicago O'Hare Intl
27h 19m
2 stops
HLN4:41 pmHelena
$504

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 August 14, 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 Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Wed 9/16

2:26 pm-10:00 pm

1 stop6h 34m

Chicago O'Hare Intl

Sat 9/19

7:00 am-1:45 pm

1 stop7h 45m

$339

HelenaChicago

HLN Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Wed 11/18

1:04 pm-11:59 pm

2 stops9h 55m

Chicago O'Hare Intl

Mon 11/23

7:35 am-12:22 pm

1 stop5h 47m

$344
Quickest round-trip

HelenaChicago

HLN Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Fri 11/6

1:08 pm-10:00 pm

1 stop7h 52m

Chicago O'Hare Intl

Sun 11/8

7:35 am-12:28 pm

1 stop5h 53m

$369

HelenaChicago

HLN Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Fri 11/6

1:08 pm-11:52 pm

2 stops9h 44m

Chicago O'Hare Intl

Sun 11/8

7:35 am-12:28 pm

1 stop5h 53m

$374

HelenaChicago

HLN Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Wed 10/14

2:30 pm-10:46 pm

1 stop7h 16m

Chicago O'Hare Intl

Sat 10/17

7:00 am-1:48 pm

1 stop7h 48m

$396

HelenaChicago

HLN Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Tue 8/25

2:35 pm-10:46 pm

1 stop7h 11m

Chicago O'Hare Intl

Sat 8/29

2:42 pm-9:30 pm

1 stop7h 48m

$409

HelenaChicago

HLN Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Tue 8/25

12:55 pm-9:33 pm

1 stop7h 38m

Chicago O'Hare Intl

Sat 8/29

6:00 am-12:15 pm

2 stops7h 15m

$414

HelenaChicago

HLN Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Fri 9/25

5:18 pm-7:21 pm

2 stops25h 03m

Chicago O'Hare Intl

Mon 9/28

6:00 am-4:41 pm

1 stop11h 41m

$462

HelenaChicago

HLN Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Fri 9/25

5:18 pm-6:20 am

1 stop12h 02m

Chicago O'Hare Intl

Sun 9/27

6:00 am-4:41 pm

1 stop11h 41m

$469

HelenaChicago

HLN Helena - ORD Chicago O'Hare Intl

HLNORD

Helena

Thu 10/15

5:26 pm-5:40 am

1 stop11h 14m

Chicago O'Hare Intl

Mon 10/19

7:16 pm-4:49 pm

1 stop22h 33m

$489

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 and Delta are the most popular carriers operating from Helena to Chicago

What airlines fly to Chicago?

United Airlines, American Airlines and Delta 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 57% 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 54m

Direct flights

None
The fastest flight from Helena to Chicago takes 5h 54m
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 54m 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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