$365 Find Cheap Flights from North Macedonia to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 9/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Flight Deals

Cheap Flights from North Macedonia to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from North Macedonia to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from North Macedonia to Chicago

Sat, Oct 10 - Sat, Nov 21
Air Serbia Logo
3:10 pm - 9:15 pm
SKP
-
ORD
13h 05m
1 stop
Air Serbia Logo
5:30 pm - 2:40 pm
ORD
-
SKP
14h 10m
1 stop
$754Air Serbia
Thu, Oct 22 - Wed, Jan 20
Multiple Airlines Logo
12:35 pm - 1:20 pm
SKP
-
ORD
31h 45m
1 stop
Multiple Airlines Logo
4:10 pm - 8:25 pm
ORD
-
SKP
21h 15m
1 stop
$764Multiple Airlines
Sun, Sep 13 - Wed, Nov 25
United Airlines Logo
4:25 am - 1:20 pm
SKP
-
ORD
15h 55m
1 stop
United Airlines Logo
4:20 pm - 11:45 am
ORD
-
SKP
12h 25m
1 stop
$767United Airlines
Wed, Sep 2 - Wed, Sep 30
Austrian Airlines Logo
12:35 pm - 1:20 pm
SKP
-
ORD
31h 45m
1 stop
Austrian Airlines Logo
12:55 pm - 11:50 am
ORD
-
SKP
15h 55m
2 stops
$770Austrian Airlines
Wed, Oct 21 - Mon, Jan 18
Multiple Airlines Logo
4:25 am - 7:51 am
SKP
-
ORD
34h 26m
2 stops
Multiple Airlines Logo
1:55 pm - 11:45 am
ORD
-
SKP
14h 50m
2 stops
$774Multiple Airlines
Thu, Oct 22 - Wed, Jan 20
Multiple Airlines Logo
12:35 pm - 1:20 pm
SKP
-
ORD
31h 45m
1 stop
Multiple Airlines Logo
7:15 am - 11:45 am
ORD
-
SKP
21h 30m
2 stops
$775Multiple Airlines
Sun, Sep 13 - Wed, Nov 25
United Airlines Logo
4:25 am - 6:37 pm
SKP
-
ORD
21h 12m
2 stops
United Airlines Logo
4:20 pm - 11:45 am
ORD
-
SKP
12h 25m
1 stop
$777United Airlines
Thu, Sep 10 - Sun, Oct 25
Austrian Airlines Logo
4:25 am - 1:20 pm
SKP
-
ORD
15h 55m
1 stop
Austrian Airlines Logo
10:50 pm - 11:45 am
ORD
-
SKP
30h 55m
2 stops
$787Austrian Airlines
Thu, Oct 22 - Wed, Jan 20
Multiple Airlines Logo
12:35 pm - 12:55 pm
SKP
-
ORD
31h 20m
2 stops
Multiple Airlines Logo
7:15 am - 11:45 am
ORD
-
SKP
21h 30m
2 stops
$792Multiple Airlines
Sun, Sep 13 - Wed, Nov 25
United Airlines Logo
4:25 am - 9:38 am
SKP
-
ORD
36h 13m
2 stops
United Airlines Logo
9:30 pm - 11:45 am
ORD
-
SKP
31h 15m
2 stops
$794United Airlines
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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago O'Hare Intl Airport is September, where tickets cost $429 on average for return flights. On the other hand, the most expensive months are August and May, where the average cost of tickets from North Macedonia is $784 and $666 respectively. For one-way flights, the best month to travel is July with an average price of $280.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 3 weeks before departure, which saves you about 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$365
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly and prices are also 16% 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 30,395 direct flights from within North Macedonia to Chicago O'Hare Intl Airport. The most common day for departures is Sunday, with 16% 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

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from North Macedonia to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 937 reviews
7.6Boarding
7.3Comfort
8.1Crew
6.8Entertainment
6.8Food
Airline reviews

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.

8.0 ExcellentAnonymous, Jun 2026
VIE - EWR
Read more Austrian Airlines reviews

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.

Absolutely the worst food I've ever had on any flight. Otherwise, the flight is OK - just your regular transatlantic economy. Condor should stop saving pennies on meals. They save a penny, lose a dollar.

This is truly the worst travel experience of my life. The UK ETA program had a technical failure, and I was stuck in limbo for 24 hours, unable to board my flight and unable to navigate anything in my itinerary. I had to rebook an entirely new flight and I’m now out doubled the money. Unconscionable.

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

Boarding by bus - this is 2026! Luggage did not board the plane though we had over two hours between flights. After it was located it didn’t fly immediately but waited one or two flights until boarding to fly yo Belgrade.

It was a great experience. The aircraft is a bit dated but other than that it was great.

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.

We were delayed three hours from Montenegro to Vienna on our outbound flight and then rebooked an extra leg on our trip to the US. Our bags, which Austrian made us check in in Montenegro even though the flight was barely half full, didn't find us for ten days. Then, when we asked for compensation for the delay we were given the runaround that the flight originated outside of the EU. Next time we fly Turkish Air.

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.

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.

Amazing crew, delicious food and drink selection. 12hr felt more like a 4hrs. Comfortable beds. Can’t wait for the new business class cabin

Flying business class saves you. Once you get out of the terminal and onto the plane, it’s fine. The traffic at the gate is a horror. No organization at all. The fact that Business class is promised early boarding is a myth.

Every time I fly LOT, I swear I will never do it again. And changing planes in Warsaw is a horror. Not even remotely organized. I can only feel sorry for the staff who have to put up with it.

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

Horrible communication, flight boarded then we sat on plane for almost 5 hours as the runway was barely covered in snow with no plows in sight and the as we tried to taxi there was a major equipment failure due to poor push off technique causing all passengers to be taken off the flight to ultimately have the flight cancelled. There was barely any communication to passengers as to what was happening or what to do next to get placed on another flight. Arriving to my final destination a whole day later having to take a connecting flight through Lisbon to ultimately end up in New York instead of a direct flight as none available for the next day. Never flying LOT airlines again!

Boarding was a madhouse. Airport staff was completely disinterested in communicating about the delays. Never again.

Smooth flight, excellent crew and good food. Not enough space; sitting are too small.

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.

Older plane with finicky seats. Crew often seem to focus on "pet" clients and over extend services to some over others. I get less attention since I'm not a regular business class client. Regardless, I've paid the money and would expect equal attention.

Our flight attendant was stellar with great anticipation and attention to details. Food was very good, and overall flight, though very long, was really good.

Be honest of what you sell: This was sold as Business Class on all three legs, while the JetBlue plane didn't even have business class seats, and wanted $164 for extra legroom seats.

Great food, and lots of it. They made us come to the gate two hours before the flight and you were stuck in the enclosure until you boarded with no bathroom or food or drink. My seat in business class was very claustrophobic, I could barely get into it and a large board blocked the window and made it even more claustrophobic

Turkish Business Class is a wonderful experience, and the best inflight dining experience I’ve had to date.

The crew was amazing and the food was really good too

Some of the best service I’ve ever seen on an international flight! The staff were super friendly and accommodating. The food was excellent with lots of choices and attention to detail. The seats are kind of old and narrow, but I have wide shoulders. The only area for improvement was making the cabin a little cooler.

It was fantastic. I really enjoyed it. It’s comfortable the flight attendant. Respect you anything you ask for they gave you except the water.

We were experiencing delayed for 4 hours and of course they took us to Turkish airlines lounge but we could not rested up since there is no bedroom. It was tiring and long day for us🙏 Especially we didn’t fly until 5:45am morning for Miami🙏😢

On Turkish it is all about the food and the service. I am overwhelmed with the quality and variety of the dining service offered on business class. I prefer the updated A350 to the older B777 cabin layout, but both are comfortable. Flights left and arrived on time with updates from the captain. I will definitely fly with them again.

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.

The seat space seemed small especially when the person ahead reclined but other than that, very good.

Luggage transfer in Chicago was not performed in time. I received my luggage at my destination two days later.

Boarding and flight itself was smooth and temperature during the flight was perfect. It was just overall vibe for long distance flight, felt cheap ( comparing to KLM or TUI that I used recently). Entertainment out of date movies with poor picture quality, no games, flight map wasn't working

Basic, 737 Boeing, business class is just an economy class seat with blocked middle seat (European standard).

Entertainment is nonexistent. Food might have been good, however due to language barriers I didn’t get to have any food. Flat bed seats and layout was excellent. Crew efficient and straightforward, but lacking any western style approach. Not that I’d expect anything else, but one could have hoped.

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

Flight took very long to even get checked in for, everything was late and written out by hand. My luggage was lost for several days and it was the most unorganized flight experience of my life.

Delaying more than 5 hours from Belgrade to Tirana Information very rude to questions

It's the shortest trip one could get from BEG anywhere, so it was fine.

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

Kraljevo is very convenient airport. It's brand new, small.and efficient. Great job!

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