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Cheap flights from Chicago to Skopje from $265

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 9/21. 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 Chicago to Skopje (CHI-SKP)

Cheap round-trip flights

Logo
6:00 pm - 2:05 pmORD-SKP
37h 05m2 stops
Logo
4:25 am - 9:55 amSKP-ORD
36h 30m2 stops
$659
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Tue, Sep 2 - Sat, Oct 11
United Airlines Logo
9:31 pm - 11:50 amORD-SKP
31h 19m2 stops
United Airlines Logo
4:25 am - 1:20 pmSKP-ORD
15h 55m1 stop
$670United Airlines
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Tue, Sep 2 - Mon, Oct 13
Turkish Airlines Logo
11:45 pm - 7:55 amORD-SKP
25h 10m1 stop
Turkish Airlines Logo
8:45 am - 9:40 amSKP-ORD
31h 55m1 stop
$704Turkish Airlines
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Wed, Oct 1 - Sun, Oct 5
Turkish Airlines Logo
11:45 pm - 7:55 amORD-SKP
25h 10m1 stop
Turkish Airlines Logo
8:45 am - 9:40 amSKP-ORD
31h 55m1 stop
$722Turkish Airlines
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Wed, Oct 1 - Mon, Oct 6
LOT Logo
2:20 pm - 4:45 pmORD-SKP
19h 25m1 stop
LOT Logo
1:35 pm - 7:40 pmSKP-ORD
13h 05m1 stop
$743LOT
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Thu, Sep 18 - Thu, Sep 25
LOT Logo
5:10 pm - 4:45 pmORD-SKP
40h 35m2 stops
LOT Logo
1:35 pm - 7:40 pmSKP-ORD
13h 05m1 stop
$752LOT
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Thu, Sep 18 - Thu, Sep 25
Austrian Airlines Logo
5:55 pm - 11:50 amORD-SKP
34h 55m2 stops
Austrian Airlines Logo
12:30 pm - 3:00 pmSKP-ORD
32h 30m1 stop
$782Austrian Airlines
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Fri, Oct 10 - Fri, Oct 31
Air Serbia Logo
11:20 pm - 2:35 pmORD-SKP
32h 15m1 stop
Air Serbia Logo
4:00 am - 9:00 pmSKP-ORD
24h 00m1 stop
$788Air Serbia
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Sat, Aug 30 - Sat, Sep 13
Austrian Airlines Logo
9:50 pm - 12:15 amORD-SKP
19h 25m2 stops
Austrian Airlines Logo
12:35 pm - 6:30 pmSKP-ORD
36h 55m2 stops
$798Austrian Airlines
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Tue, Sep 2 - Fri, Oct 10
Air Serbia Logo
11:20 pm - 2:35 pmORD-SKP
32h 15m1 stop
Air Serbia Logo
4:00 am - 4:40 pmSKP-ORD
19h 40m1 stop
$853Air Serbia
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Sat, Aug 30 - Mon, Sep 15

Turkish Airlines flights from Chicago to Skopje

Our best Turkish Airlines deals on Chicago to Skopje flight tickets
Turkish Airlines
Oct 1
ORD11:45 pmChicago O'Hare Intl
25h 10m
1 stop
SKP7:55 amSkopje
Oct 5
SKP8:45 amSkopje
31h 55m
1 stop
ORD9:40 amChicago O'Hare Intl
$704
Find similar
Turkish Airlines
Oct 1
ORD11:45 pmChicago O'Hare Intl
25h 10m
1 stop
SKP7:55 amSkopje
Oct 6
SKP8:45 amSkopje
31h 55m
1 stop
ORD9:40 amChicago O'Hare Intl
$722
Find similar
Turkish Airlines
Oct 11
ORD11:45 pmChicago O'Hare Intl
25h 10m
1 stop
SKP7:55 amSkopje
Nov 3
SKP9:15 amSkopje
16h 10m
1 stop
ORD6:25 pmChicago O'Hare Intl
$732
Find similar

SWISS flights from Chicago to Skopje

Our best SWISS deals on Chicago to Skopje flight tickets
SWISS
Oct 14
ORD7:05 pmChicago O'Hare Intl
17h 40m
1 stop
SKP7:45 pmSkopje
Oct 31
SKP8:55 amSkopje
35h 50m
2 stops
ORD2:45 pmChicago O'Hare Intl
$769
Find similar
SWISS
Oct 11
ORD6:00 pmChicago O'Hare Intl
43h 05m
2 stops
SKP8:05 pmSkopje
Nov 3
SKP8:45 pmSkopje
51h 15m
2 stops
ORD5:00 pmChicago O'Hare Intl
$773
Find similar
SWISS
Oct 13
ORD8:20 pmChicago O'Hare Intl
40h 25m
2 stops
SKP7:45 pmSkopje
Nov 3
SKP8:45 pmSkopje
51h 15m
2 stops
ORD5:00 pmChicago O'Hare Intl
$775
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 August 21, 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 9/2

6:00 pm-2:05 pm

2 stops37h 05m

Skopje

Sat 10/11

4:25 am-9:55 am

2 stops36h 30m

$659

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 9/2

9:31 pm-11:50 am

2 stops31h 19m

Skopje

Mon 10/13

4:25 am-1:20 pm

1 stop15h 55m

$670

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 10/1

11:45 pm-7:55 am

1 stop25h 10m

Skopje

Sun 10/5

8:45 am-9:40 am

1 stop31h 55m

$704

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Wed 10/1

11:45 pm-7:55 am

1 stop25h 10m

Skopje

Mon 10/6

8:45 am-9:40 am

1 stop31h 55m

$722

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Thu 9/18

2:20 pm-4:45 pm

1 stop19h 25m

Skopje

Thu 9/25

1:35 pm-7:40 pm

1 stop13h 05m

$743

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Thu 9/18

5:10 pm-4:45 pm

2 stops40h 35m

Skopje

Thu 9/25

1:35 pm-7:40 pm

1 stop13h 05m

$752

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Fri 10/10

5:55 pm-11:50 am

2 stops34h 55m

Skopje

Fri 10/31

12:30 pm-3:00 pm

1 stop32h 30m

$782

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 8/30

11:20 pm-2:35 pm

1 stop32h 15m

Skopje

Sat 9/13

4:00 am-9:00 pm

1 stop24h 00m

$788

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Tue 9/2

9:50 pm-12:15 am

2 stops19h 25m

Skopje

Fri 10/10

12:35 pm-6:30 pm

2 stops36h 55m

$798

ChicagoSkopje

ORD - SKP

ORDSKP

Chicago O'Hare Intl

Sat 8/30

11:20 pm-2:35 pm

1 stop32h 15m

Skopje

Mon 9/15

4:00 am-4:40 pm

1 stop19h 40m

$853

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 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 typical price of a round-trip flight between Chicago and Skopje?

What is the cheapest month to fly to Skopje?

The month of October is, on average, the cheapest month to fly to Skopje from Chicago, with most prices found around $517. The month of March is another great option to travel to Skopje, with average flight prices from Chicago averaging around $536.

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 $780 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 $779 on momondo.

How have Chicago to Skopje flight prices changed over time?

As of August 2025, prices for Chicago to Skopje flights are approximately 44% 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.
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  • 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
SWISSPriceFrom $493Free CancellationRating
7.6
1,702 reviews
Search SWISS flights
Turkish AirlinesPriceFrom $508Free CancellationRating
7.3
3,950 reviews
Search Turkish Airlines flights
United AirlinesPriceFrom $520Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights
Austrian AirlinesPriceFrom $549Free CancellationRating
7.6
832 reviews
Search Austrian Airlines flights
LufthansaPriceFrom $559Free CancellationRating
6.8
7,344 reviews
Search Lufthansa flights
Air SerbiaPriceFrom $579Free CancellationRating
6.2
198 reviews
Search Air Serbia flights
LOTPriceFrom $622Free CancellationRating
7.6
1,110 reviews
Search LOT 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.

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