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Cheap Flights from North Macedonia to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from North Macedonia to Chicago

Thu, Sep 10 - Fri, Oct 23
LOT Logo
1:35 pm - 3:10 pmSKP  Skopje-ORD Chicago O'Hare Intl
32h 35m2 stops Warsaw Frederic Chopin Krakow J. Paul II Balice
LOT Logo
5:10 pm - 4:45 pmORD  Chicago O'Hare Intl-SKP Skopje
16h 35m1 stop Warsaw Frederic Chopin
$773LOT
Fri, Sep 18 - Sat, Sep 19
United Airlines Logo
4:25 am - 1:20 pmSKP  Skopje-ORD Chicago O'Hare Intl
15h 55m1 stop Vienna Intl
United Airlines Logo
7:05 am - 11:50 amORD  Chicago O'Hare Intl-SKP Skopje
21h 45m2 stops Newark Vienna Intl
$778United Airlines
Wed, Sep 30 - Tue, Nov 24
Multiple Airlines Logo
6:15 am - 7:15 pmSKP  Skopje-ORD Chicago O'Hare Intl
20h 00m2 stops Berlin Brandenburg Dublin
Multiple Airlines Logo
1:55 pm - 8:25 pmORD  Chicago O'Hare Intl-SKP Skopje
47h 30m2 stops Montreal Pierre Elliott Trudeau Intl Zurich
$805Multiple Airlines
Fri, Oct 2 - Fri, Oct 9
Austrian Airlines Logo
4:25 am - 1:20 pmSKP  Skopje-ORD Chicago O'Hare Intl
15h 55m1 stop Vienna Intl
Austrian Airlines Logo
4:20 pm - 11:50 amORD  Chicago O'Hare Intl-SKP Skopje
12h 30m1 stop Vienna Intl
$811Austrian Airlines
Wed, Dec 23 - Sat, Jan 9
Air Serbia Logo
3:10 pm - 9:20 pmSKP  Skopje-ORD Chicago O'Hare Intl
13h 10m1 stop Belgrade Nikola Tesla
Air Serbia Logo
5:30 pm - 2:05 amORD  Chicago O'Hare Intl-SKP Skopje
25h 35m1 stop Belgrade Nikola Tesla
$814Air Serbia
Fri, Oct 2 - Thu, Oct 22
Multiple Airlines Logo
4:25 am - 1:20 pmSKP  Skopje-ORD Chicago O'Hare Intl
15h 55m1 stop Vienna Intl
Multiple Airlines Logo
7:05 pm - 7:55 pmORD  Chicago O'Hare Intl-SKP Skopje
17h 50m1 stop Zurich
$818Multiple Airlines
Fri, Oct 2 - Fri, Oct 9
Austrian Airlines Logo
4:25 am - 1:20 pmSKP  Skopje-ORD Chicago O'Hare Intl
15h 55m1 stop Vienna Intl
Austrian Airlines Logo
4:20 pm - 11:50 amORD  Chicago O'Hare Intl-SKP Skopje
12h 30m1 stop Vienna Intl
$821Austrian Airlines
Tue, Nov 10 - Sat, Nov 21
United Airlines Logo
4:30 am - 2:00 pmSKP  Skopje-ORD Chicago O'Hare Intl
16h 30m1 stop Vienna Intl
United Airlines Logo
4:20 pm - 11:45 amORD  Chicago O'Hare Intl-SKP Skopje
12h 25m1 stop Vienna Intl
$842United Airlines
Wed, Dec 23 - Mon, Jan 4
Turkish Airlines Logo
8:45 am - 6:20 pmSKP  Skopje-ORD Chicago O'Hare Intl
16h 35m1 stop Istanbul
Turkish Airlines Logo
11:45 am - 7:55 pmORD  Chicago O'Hare Intl-SKP Skopje
25h 10m1 stop Istanbul
$843Turkish Airlines
Sun, Sep 13 - Sat, Feb 13
Air Serbia Logo
3:10 pm - 2:30 pmSKP  Skopje-ORD Chicago O'Hare Intl
30h 20m1 stop Belgrade Nikola Tesla
Air Serbia Logo
5:30 pm - 2:35 pmORD  Chicago O'Hare Intl-SKP Skopje
14h 05m1 stop Belgrade Nikola Tesla
$932Air Serbia
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The cheapest month for flights to Chicago O'Hare Intl Airport is December, where tickets cost $677 on average for return flights. On the other hand, the most expensive months are August and February, where the average cost of tickets from North Macedonia is $1,095 and $1,017 respectively. For one-way flights, the best month to travel is November with an average price of $538.

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

To get a below average price, you should book around 3 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low season

August

Cheapest flight

$342
Best time to beat the crowds but there is an average 34% increase in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Skopje to Chicago

FAQs - booking Chicago flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    Central Chicago is 16 miles away from Chicago O'Hare Intl Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago O'Hare Intl Airport are there each week?

    Each week there are around 29,223 direct flights from within North Macedonia to Chicago O'Hare Intl Airport. The most common day for departures is Sunday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top 5 airlines serving from North Macedonia to Chicago

 
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.6
Austrian AirlinesOverall score based on 949 reviews
7.3Comfort
6.8Entertainment
6.8Food
7.6Boarding
8.1Crew
Airline reviews

No way to add a bag without getting in line at the counter, which took at least half an hour. No WiFi.

6.0 GoodBecky, Jul 2026
Read more Austrian Airlines reviews

No way to add a bag without getting in line at the counter, which took at least half an hour. No WiFi.

The preboarding and the gate organizing management was poor, unorganized and mismanaged. While standing in the business line I kept getting ignored and the personnel kept checking in others, right in front of me until I finally spoke up and pointed out their clear signs of ignoring me while patiently waiting to be checked in. Once checked in the gate the personnel kept chit-chatting and not managing which group is to board, being totally nonchalant, unorganized and behaving amateur-like . Very unprofessional and unlike the quality the Austrian Airlines brand otherwise provides. The crew on the plane are always fantastic and the best. What a shame the crew on the ground was so mediocre.

Flight delayed with no explanation. Boarding was confused (proceed to plane, go back to waiting area).

Last few years I didn't not have great experience with United Airlines.

Short flight. Bare bones and kinda seeming like an older plane. But got me there on time and that's what counts. Perfectly fine flight all the way from start to finish.

My Austrian Air flight from Montenegro to Vienna was delayed by three hours because their plane de-icer was broken and they had to wait for the sun to come up before the ice could melt. This meant we missed our United flight altogether. So I can't speak about United, but I was not impressed by Austrian Air. They made us check in two carry on bags for a 60% full flight, and the bags didn't find us in the US for ten days. The re-routing they arranged included an extra leg, a midnight taxi ride across New Jersey and New York, and a five hour sleep in a hotel. Not impressed.

Excellent flight. The crew was exceptionally attentive and organized. Attention to details is unmatched.

I been flying with Austrian for few years, they never failed me.

Vienna airport is a zoo Agents directed me to the wrong gate and then the wrong line Lounge is so crowded no place to sit Not enough bathrooms anywhere On the flight they asked for medical attention While I attended to the problem they forgot my food when I got back They forgot to give me water at night Waited 1 hour for bags Agents didn’t know which Shute the bags were coming to so it was between 2 places

Food: my selection was pasta with vegetables, though it was potatoes not pasta. Breakfast was 2 rolls and some sort of spreads— not sure what they were. Worst thing was that we had to wait for over 90 minutes for our bags to show up at O’Hare

I have flown with LOT several times and regret it every time; however, they are the only airline that offers the direct flights I need. Boarding was awful. I was alone with 3 children, including an infant, and we were forced to stand in buses packed like sardines. Then, for such a large flight, there was not even a gangway. I was expected to carry a baby, a carseat, and luggage by myself up the dangerous steps into the plane while the crew RUSHED me. The crew was very curt, cold, and inattentive. No one offered any assistance or sympathy to me alone with kids. There was no ventilation or AC in the plane.

My ONLY complaint with LOT was the lack of WiFi and the food in business class… still, I use them because they have great connections to Chicago and they fly the 787 - which I think is a great wide body jet. Well… now LOT has WiFi (good satellite speeds) and AMAZING food. LOT now is giving Turkish Airlines a big big run for the money. And they consistently have less expensive business class. I am a very happy customer!

Issue with boarding, group of passengers on a religious trip coming back to NYC kept trying to change seats, even standing when the plane was pushing back. Crew/Pilot kept very good composure, some passengers got aggravated and started venting out loud but this group created a serious security risk. Crew/Pilot should've been more stringent and called in security or remove them from the flight.

The seat was paid for but given for some different person .

Krakow airport is very disorganized. nice seats. friendly crew. long legs had screens. short leg did not

Flight was delayed for a hour from Warsaw, not sure why. When we landed in Chicago, plane was still on the runway for about half a hour. Took a while to get off.

No WiFi and ok comfort in business class. Home safe I guess that’s all that really matters.

I would like to be able to choose the seat before the flight without paying extra money. Family members should not to be separated from each other.

Flight was delayed by a hour could have been better addressed. Flight was fine with great service by the flight attendants

All good. Didn’t get the seats I booked online. Luckily, copassanger cooperated! Mistake- I failed to verify connecting flight seats details at Mumbai. Staff at Mumbai airport to be blamed equally!

Horrible service at the baggage claim. Stuck on plane for an hour due to taxing and no gate.

I really would like it if they provided at least some limited free wi-fi.

Excellent food and service on my international flight. Most notable is the food provided by Turkish even for coach passengers is very good.

Food is very turkish. No regard for other natinalities taste and preference. The entertainment can be improved- it was the same menu on 10/8/25 and 10/25/25. The boarding is the worst in the airline industry- I suggest you ask your staff to and watch how other airlines do it.

We couldn’t fly to Chicago on our booked flight. The flight was overbooked.

Took forever to board. They made announcements without the loudspeaker and since the waiting room was full of screaming kids, no one could hear what they were saying. The business class sleeper seats were designed for tall skinny people. When partially reclined there was nowhere to rest my feet because they did not reach the footrest. and when fully reclined there wasn't room at my sides for my arms. Definitely one of the worst sleeper seats I have ever had.

About an hour delay but we made it to Chicago. I feel that the smaller connecting flights are the ones that cause the delays on the bigger planes that fly international.

One of the best flights I have been on in a while.

Here's a sample answer: "Honestly, I was really impressed with Turkish Airlines, but if I had to suggest one area for improvement, it would be: - *More efficient boarding process*: I noticed that boarding took a bit longer than expected, which might be frustrating for passengers with tight connections.

Not worth pay business class and get service economy class

the blanket was great and pillow helped. really need a toothpick packed with meals

Very comfortable plane. The food was very good (for airplane food). The crew was great

The legroom was lacking and the entertainment system lacked adequate selection of older films. Modern films are generally not very good.

Perfect airline, super friendly, great service, tasty food. Would fly again.

Everything could have been better. What needed to be wrong with United went wrong

It was good. The seats in economy weren’t bad

Very good. Comfortable and I felt well taken care of from start to finish

We were in premium economy seats that appeared to be locked in plae, No reclining. My aching back.

I don’t understand how they charge as much as they do for such a poor experience

I wish the plane had pod seating for business class. I had a window seat (8K) and I had to climb over the person sitting on the aisle when I needed to get up. Also there is no partition between the seats for privacy when sleeping. The Asian airlines have much nicer business class seating. Their seats are wider for better comfort when sleeping.

Unorganized, late and they lost my bag for several days.

I paid for luggage when I bought the ticket but I could not board until I paid for luggage again. The fault lays at the feet of eDreams, the company that booked our flight. Sorry, Air Serbia, but it did affect the boarding process.

They had lost my ticket and despite showing them the confirmation email with the itinerary and receipt of payment for the flight they could not put me on that flight and rescheduled departure postponing it by a whole week

Long delay (6 hour late departure, not informative enough to provide up to date info on flight, poor food quality

Plane was late causing me to miss connection. Flight the next late causing me to miss the rebooked connection. Air seberia I think is more late than on time

Plane was old. Seats were hard and very close together. No in flight entertainment.

This was my connection flight that was moved time ahead for a almost entire day so I lost it and I had to purchase new ticket once I landed in Copenhagen since nobody wanted to take responsibility for moving flight in that way so it’s impossible to make it. Very poor job by Underpricer, Air Serbia and SAS.

This flight was better, plane was newer and didn’t have broken parts. Flight crew was very attentive and friendly.

Seats are very small and uncomfortable so such a long flight. My tray table was broken and taped up. Flight attendant untaped it to put my tray on. I taped it back up when done. The armrest between seats was broken and metal exposed. I will not book Air Serbia again.

To be honest, it was a fair flight, nothing more, nothing less. Since the route is short, I can accept poor in-flight service. The Belgrade airport is currently undergoing extensive reconstruction, which may result in some minor disruptions, but progress is expected to be made within the foreseeable future.

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