Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Skopje from $274

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Skopje departing on 10/5. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Skopje

Cheap round-trip flights

Austrian Airlines Logo
4:20 pm - 12:15 amORD-SKP
24h 55m1 stop
Austrian Airlines Logo
12:30 pm - 3:00 pmSKP-ORD
32h 30m1 stop
$580Austrian Airlines
Find Deal
Tue, Oct 14 - Thu, Oct 30
Multiple Airlines Logo
6:50 pm - 7:45 pmORD-SKP
17h 55m1 stop
Multiple Airlines Logo
5:40 am - 1:01 pmSKP-ORD
38h 21m2 stops
$581Multiple Airlines
Find Deal
Sat, Nov 15 - Sat, Nov 29
Lufthansa Logo
4:00 pm - 11:50 amORD-SKP
12h 50m2 stops
Lufthansa Logo
4:30 am - 1:10 pmSKP-ORD
15h 40m2 stops
$582Lufthansa
Find Deal
Fri, Oct 10 - Sun, Nov 2
Lufthansa Logo
10:35 pm - 10:20 pmORD-SKP
16h 45m1 stop
Lufthansa Logo
12:30 pm - 6:25 pmSKP-ORD
36h 55m2 stops
$583Lufthansa
Find Deal
Sun, Dec 28 - Fri, Jan 16
United Airlines Logo
7:30 am - 11:50 amORD-SKP
21h 20m2 stops
United Airlines Logo
4:30 am - 3:00 pmSKP-ORD
16h 30m1 stop
$584United Airlines
Find Deal
Wed, Oct 1 - Sat, Nov 1
LOT Logo
9:40 pm - 4:45 pmORD-SKP
12h 05m1 stop
LOT Logo
5:30 pm - 7:40 pmSKP-ORD
33h 10m1 stop
$590LOT
Find Deal
Thu, Oct 2 - Wed, Oct 15
United Airlines Logo
11:45 am - 11:50 amORD-SKP
17h 05m2 stops
United Airlines Logo
4:30 am - 8:07 pmSKP-ORD
21h 37m2 stops
$594United Airlines
Find Deal
Wed, Oct 1 - Sat, Nov 1
LOT Logo
5:10 pm - 4:45 pmORD-SKP
40h 35m2 stops
LOT Logo
5:30 pm - 7:40 pmSKP-ORD
33h 10m1 stop
$601LOT
Find Deal
Thu, Oct 2 - Wed, Oct 15
SWISS Logo
7:05 pm - 7:45 pmORD-SKP
17h 40m1 stop
SWISS Logo
8:50 pm - 3:55 pmSKP-ORD
26h 05m1 stop
$603SWISS
Find Deal
Tue, Sep 30 - Mon, Oct 6
SWISS Logo
6:50 pm - 7:55 pmORD-SKP
18h 05m1 stop
SWISS Logo
8:55 am - 4:20 pmSKP-ORD
14h 25m1 stop
$618SWISS
Find Deal
Sun, Dec 28 - Fri, Jan 16

United Airlines flights from Chicago to Skopje

Our best United Airlines deals on Chicago to Skopje flight tickets
United Airlines
Oct 1
ORD7:30 amChicago O'Hare Intl
21h 20m
2 stops
SKP11:50 amSkopje
Nov 1
SKP4:30 amSkopje
16h 30m
1 stop
ORD3:00 pmChicago O'Hare Intl
$584
Find similar
United Airlines
Oct 1
ORD11:45 amChicago O'Hare Intl
17h 05m
2 stops
SKP11:50 amSkopje
Nov 1
SKP4:30 amSkopje
21h 37m
2 stops
ORD8:07 pmChicago O'Hare Intl
$594
Find similar
United Airlines
Oct 15
ORD9:20 pmChicago O'Hare Intl
31h 30m
2 stops
SKP11:50 amSkopje
Oct 29
SKP4:30 amSkopje
16h 30m
1 stop
ORD3:00 pmChicago O'Hare Intl
$595
Find similar

Lufthansa flights from Chicago to Skopje

Our best Lufthansa deals on Chicago to Skopje flight tickets
Lufthansa
Oct 10
ORD4:00 pmChicago O'Hare Intl
12h 50m
2 stops
SKP11:50 amSkopje
Nov 2
SKP4:30 amSkopje
15h 40m
2 stops
ORD1:10 pmChicago O'Hare Intl
$582
Find similar
Lufthansa
Dec 28
ORD10:35 pmChicago O'Hare Intl
16h 45m
1 stop
SKP10:20 pmSkopje
Jan 16
SKP12:30 pmSkopje
36h 55m
2 stops
ORD6:25 pmChicago O'Hare Intl
$583
Find similar
Lufthansa
Dec 26
ORD7:55 pmChicago O'Hare Intl
36h 40m
2 stops
SKP3:35 pmSkopje
Jan 15
SKP12:30 pmSkopje
31h 40m
2 stops
ORD1:10 pmChicago O'Hare Intl
$587
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Skopje 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 September 17, 2025.
Use the filters below to find and compare flights from Chicago to Skopje that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 10/14

4:20 pm-12:15 am

1 stop24h 55m

Skopje

Thu 10/30

12:30 pm-3:00 pm

1 stop32h 30m

$580

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 11/15

6:50 pm-7:45 pm

1 stop17h 55m

Skopje

Sat 11/29

5:40 am-1:01 pm

2 stops38h 21m

$581

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 10/10

4:00 pm-11:50 am

2 stops12h 50m

Skopje

Sun 11/2

4:30 am-1:10 pm

2 stops15h 40m

$582

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 12/28

10:35 pm-10:20 pm

1 stop16h 45m

Skopje

Fri 1/16

12:30 pm-6:25 pm

2 stops36h 55m

$583

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 10/1

7:30 am-11:50 am

2 stops21h 20m

Skopje

Sat 11/1

4:30 am-3:00 pm

1 stop16h 30m

$584

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Thu 10/2

9:40 pm-4:45 pm

1 stop12h 05m

Skopje

Wed 10/15

5:30 pm-7:40 pm

1 stop33h 10m

$590

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 10/1

11:45 am-11:50 am

2 stops17h 05m

Skopje

Sat 11/1

4:30 am-8:07 pm

2 stops21h 37m

$594

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Thu 10/2

5:10 pm-4:45 pm

2 stops40h 35m

Skopje

Wed 10/15

5:30 pm-7:40 pm

1 stop33h 10m

$601

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 9/30

7:05 pm-7:45 pm

1 stop17h 40m

Skopje

Mon 10/6

8:50 pm-3:55 pm

1 stop26h 05m

$603

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sun 12/28

6:50 pm-7:55 pm

1 stop18h 05m

Skopje

Fri 1/16

8:55 am-4:20 pm

1 stop14h 25m

$618

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Skopje from

How to get the cheapest flight ticket from Chicago to Skopje

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 month to fly to Skopje?

The month of January is, on average, the cheapest month to fly to Skopje from Chicago, with most prices found around $544. The month of March is another great option to travel to Skopje, with average flight prices from Chicago averaging around $544.

What is the cheapest day to depart on your flight to Skopje?

Our data shows that Friday is the least expensive day to fly to Skopje. Tickets to fly out on this day can be as low as $928. Flights from Chicago to Skopje on a Thursday will generally be more expensive and average around $1,140. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Skopje?

According to our data, the cheapest time of day to fly to Skopje is in the morning. momondo users have found flights departing from Chicago to Skopje in the morning for as low as $907. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $1,152 on average. Flights to Skopje from Chicago in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

How far in advance should I book a flight to Skopje?

You are more likely to see cheaper flights to Skopje from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Skopje for around $766 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Skopje from Chicago for as low as $781 on momondo.

How have Chicago to Skopje flight prices changed over time?

As of September 2025, prices for Chicago to Skopje flights are approximately 6% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Skopje

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

Cheap Chicago to Skopje (CHI to SKP) flight deals and tips

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

Direct flights

None
There are no direct flights from Chicago to Skopje. There are no popular flight routes from Chicago to Skopje.
Search flight deals

  • How far is Chicago to Skopje by plane?

    The straight-line distance from Chicago to Skopje is 5149.8 mi. Flights usually cover this in 12h 05m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago to Skopje Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Skopje Airport?

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Skopje Airport.

  • What documentation or ID do you need to fly to Skopje Airport?

    The travel and health documents required for your trip to Skopje Airport 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 Skopje Airport. 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 Chicago to Skopje?

Best airlines flying from Chicago to Skopje

Compare and see reviews for airlines that fly from Chicago to Skopje with momondo
Airline
Rating
Free Cancellation
Price
Turkish AirlinesPriceFrom $509Free CancellationRating
7.3
3,965 reviews
Search Turkish Airlines flights
United AirlinesPriceFrom $521Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
Austrian AirlinesPriceFrom $567Free CancellationRating
7.6
850 reviews
Search Austrian Airlines flights
LufthansaPriceFrom $571Free CancellationRating
6.8
7,409 reviews
Search Lufthansa flights
Air SerbiaPriceFrom $580Free CancellationRating
6.2
200 reviews
Search Air Serbia flights
LOTPriceFrom $623Free CancellationRating
7.6
1,117 reviews
Search LOT flights
SWISSPriceFrom $640Free CancellationRating
7.6
1,737 reviews
Search SWISS flights

Why use momondo?

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

Finding the right flight to Skopje from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Skopje quick and easy, saving you time and money.

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

Flights from Chicago to Skopje with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo provides multiple filters to help you find the best flight to Skopje from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Skopje from Chicago 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.

An easier way to manage your Skopje trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 10/17
Fri 10/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to North Macedonia

Airports servicing North Macedonia

Ohrid Airport