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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 4/16. 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

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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.
Alaska Airlines Logo
6:22 pm - 6:40 am
HLN
-
ORD
11h 18m
1 stop
Alaska Airlines Logo
6:00 am - 5:45 pm
ORD
-
HLN
12h 45m
1 stop
$349Alaska Airlines
Sat, May 9 - Tue, May 12
United Airlines Logo
2:30 pm - 9:23 pm
HLN
-
ORD
5h 53m
1 stop
United Airlines Logo
2:20 pm - 9:46 pm
ORD
-
HLN
8h 26m
1 stop
$369United Airlines
Sat, May 9 - Tue, May 12
Delta Logo
5:45 am - 8:14 pm
HLN
-
ORD
13h 29m
2 stops
Delta Logo
7:45 am - 12:23 pm
ORD
-
HLN
5h 38m
1 stop
$370Delta
Sat, May 9 - Tue, May 12
Delta Logo
5:45 am - 11:52 am
HLN
-
ORD
5h 07m
1 stop
Delta Logo
7:45 am - 12:23 pm
ORD
-
HLN
5h 38m
1 stop
$382Delta
Sat, May 9 - Wed, May 13
Alaska Airlines Logo
6:22 pm - 6:40 am
HLN
-
ORD
11h 18m
1 stop
Alaska Airlines Logo
8:48 pm - 5:45 pm
ORD
-
HLN
21h 57m
1 stop
$383Alaska Airlines
Thu, Apr 30 - Mon, May 4
Delta Logo
1:03 pm - 9:50 pm
HLN
-
ORD
7h 47m
1 stop
Delta Logo
7:45 am - 12:23 pm
ORD
-
HLN
5h 38m
1 stop
$385Delta
Fri, May 8 - Tue, May 12
Delta Logo
5:45 am - 8:14 pm
HLN
-
ORD
13h 29m
2 stops
Delta Logo
7:45 am - 12:23 pm
ORD
-
HLN
5h 38m
1 stop
$387Delta
Sat, May 9 - Wed, May 13
Delta Logo
5:45 am - 8:14 pm
HLN
-
ORD
13h 29m
2 stops
Delta Logo
7:45 am - 12:23 pm
ORD
-
HLN
5h 38m
1 stop
$390Delta
Sat, May 9 - Tue, May 12
Alaska Airlines Logo
6:22 pm - 6:40 am
HLN
-
ORD
11h 18m
1 stop
Alaska Airlines Logo
8:48 pm - 5:45 pm
ORD
-
HLN
21h 57m
1 stop
$394Alaska Airlines
Thu, Apr 30 - Mon, May 4
United Airlines Logo
2:25 pm - 9:20 pm
HLN
-
ORD
5h 55m
1 stop
United Airlines Logo
4:10 pm - 9:33 pm
ORD
-
HLN
6h 23m
1 stop
$399United Airlines
Tue, Apr 21 - Sat, Apr 25

Delta flights from Helena to Chicago

Our best Delta deals on Helena to Chicago flight tickets
Delta
Sep 3
HLN12:50 pmHelena
8h 08m
1 stop
ORD9:58 pmChicago O'Hare Intl
Sep 8
ORD7:30 amChicago O'Hare Intl
5h 53m
1 stop
HLN12:23 pmHelena
$365
Delta
May 9
HLN5:45 amHelena
13h 29m
2 stops
ORD8:14 pmChicago O'Hare Intl
May 12
ORD7:45 amChicago O'Hare Intl
5h 38m
1 stop
HLN12:23 pmHelena
$370
Delta
May 9
HLN5:45 amHelena
5h 07m
1 stop
ORD11:52 amChicago O'Hare Intl
May 13
ORD7:45 amChicago O'Hare Intl
5h 38m
1 stop
HLN12:23 pmHelena
$382

Alaska Airlines flights from Helena to Chicago

Our best Alaska Airlines deals on Helena to Chicago flight tickets
Alaska Airlines
May 9
HLN6:22 pmHelena
11h 18m
1 stop
ORD6:40 amChicago O'Hare Intl
May 12
ORD6:00 amChicago O'Hare Intl
12h 45m
1 stop
HLN5:45 pmHelena
$349
Alaska Airlines
Apr 30
HLN6:22 pmHelena
11h 18m
1 stop
ORD6:40 amChicago O'Hare Intl
May 4
ORD8:48 pmChicago O'Hare Intl
21h 57m
1 stop
HLN5:45 pmHelena
$383
Alaska Airlines
Apr 30
HLN6:22 pmHelena
11h 18m
1 stop
ORD6:40 amChicago O'Hare Intl
May 4
ORD8:48 pmChicago O'Hare Intl
21h 57m
1 stop
HLN5:45 pmHelena
$394

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 April 11, 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

Sat 5/9

6:22 pm-6:40 am

1 stop11h 18m

Chicago O'Hare Intl

Tue 5/12

6:00 am-5:45 pm

1 stop12h 45m

$349

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 5/9

2:30 pm-9:23 pm

1 stop5h 53m

Chicago O'Hare Intl

Tue 5/12

2:20 pm-9:46 pm

1 stop8h 26m

$369

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 5/9

5:45 am-8:14 pm

2 stops13h 29m

Chicago O'Hare Intl

Tue 5/12

7:45 am-12:23 pm

1 stop5h 38m

$370
Quickest round-trip

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 5/9

5:45 am-11:52 am

1 stop5h 07m

Chicago O'Hare Intl

Wed 5/13

7:45 am-12:23 pm

1 stop5h 38m

$382

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 4/30

6:22 pm-6:40 am

1 stop11h 18m

Chicago O'Hare Intl

Mon 5/4

8:48 pm-5:45 pm

1 stop21h 57m

$383

HelenaChicago

HLN - ORD

HLNORD

Helena

Fri 5/8

1:03 pm-9:50 pm

1 stop7h 47m

Chicago O'Hare Intl

Tue 5/12

7:45 am-12:23 pm

1 stop5h 38m

$385

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 5/9

5:45 am-8:14 pm

2 stops13h 29m

Chicago O'Hare Intl

Wed 5/13

7:45 am-12:23 pm

1 stop5h 38m

$387

HelenaChicago

HLN - ORD

HLNORD

Helena

Sat 5/9

5:45 am-8:14 pm

2 stops13h 29m

Chicago O'Hare Intl

Tue 5/12

7:45 am-12:23 pm

1 stop5h 38m

$390

HelenaChicago

HLN - ORD

HLNORD

Helena

Thu 4/30

6:22 pm-6:40 am

1 stop11h 18m

Chicago O'Hare Intl

Mon 5/4

8:48 pm-5:45 pm

1 stop21h 57m

$394

HelenaChicago

HLN - ORD

HLNORD

Helena

Tue 4/21

2:25 pm-9:20 pm

1 stop5h 55m

Chicago O'Hare Intl

Sat 4/25

4:10 pm-9:33 pm

1 stop6h 23m

$399

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, United Airlines, and Delta 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 47% 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 07m

Direct flights

None
The fastest flight from Helena to Chicago takes 5h 07m
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 07m 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
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?

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