$415 Find Cheap Flights from North Macedonia to Chicago

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 4/20. 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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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

Fri, May 8 - Tue, Sep 1
Multiple Airlines Logo
5:45 am - 9:25 pm
SKP
-
ORD
22h 40m
2 stops
Multiple Airlines Logo
7:25 pm - 12:50 am
ORD
-
SKP
22h 25m
2 stops
$568Multiple Airlines
Thu, Jul 2 - Thu, Aug 6
Turkish Airlines Logo
8:45 am - 9:40 am
SKP
-
ORD
31h 55m
1 stop
Turkish Airlines Logo
11:25 am - 7:25 pm
ORD
-
SKP
25h 00m
1 stop
$653Turkish Airlines
Fri, May 8 - Tue, Sep 1
Turkish Airlines Logo
8:45 am - 9:40 am
SKP
-
ORD
31h 55m
1 stop
Turkish Airlines Logo
11:25 am - 7:55 am
ORD
-
SKP
13h 30m
1 stop
$654Turkish Airlines
Fri, Apr 17 - Mon, Apr 27
Turkish Airlines Logo
8:45 am - 9:40 am
SKP
-
ORD
31h 55m
1 stop
Turkish Airlines Logo
11:25 am - 7:25 pm
ORD
-
SKP
25h 00m
1 stop
$656Turkish Airlines
Mon, Apr 20 - Wed, Sep 16
Turkish Airlines Logo
8:45 am - 9:40 am
SKP
-
ORD
31h 55m
1 stop
Turkish Airlines Logo
11:25 am - 7:55 am
ORD
-
SKP
13h 30m
1 stop
$658Turkish Airlines
Fri, Apr 17 - Mon, Apr 27
Turkish Airlines Logo
8:45 am - 9:40 am
SKP
-
ORD
31h 55m
1 stop
Turkish Airlines Logo
8:10 pm - 7:25 pm
ORD
-
SKP
16h 15m
1 stop
$659Turkish Airlines
Sat, Apr 18 - Tue, Apr 28
Turkish Airlines Logo
8:15 pm - 9:40 am
SKP
-
ORD
20h 25m
1 stop
Turkish Airlines Logo
11:25 am - 7:55 am
ORD
-
SKP
13h 30m
1 stop
$662Turkish Airlines
Thu, Jun 4 - Mon, Aug 10
Turkish Airlines Logo
8:45 am - 9:40 am
SKP
-
ORD
31h 55m
1 stop
Turkish Airlines Logo
11:25 am - 7:25 pm
ORD
-
SKP
25h 00m
1 stop
$677Turkish Airlines
Wed, May 6 - Sun, Aug 30
Turkish Airlines Logo
8:15 pm - 9:40 am
SKP
-
ORD
20h 25m
1 stop
Turkish Airlines Logo
11:25 am - 7:55 am
ORD
-
SKP
13h 30m
1 stop
$680Turkish Airlines
Wed, Jun 24 - Wed, Sep 9
Turkish Airlines Logo
8:15 pm - 9:40 am
SKP
-
ORD
20h 25m
1 stop
Turkish Airlines Logo
8:10 pm - 7:25 pm
ORD
-
SKP
16h 15m
1 stop
$681Turkish 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 flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Skopje, at $568 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $114 in the last 3 days.

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 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 November, where tickets cost $637 on average for return flights. On the other hand, the most expensive months are February and August, where the average cost of tickets from North Macedonia is $1,017 and $853 respectively. For one-way flights, the best month to travel is November with an average price of $637.

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 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$415
Best time to beat the crowds but there is an average 34% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Skopje to Chicago

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Skopje, at $568 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $114 in the last 3 days.

  • 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 11,422 direct flights from within North Macedonia to Chicago O'Hare Intl Airport. The most common day for departures is Thursday, 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

 
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 905 reviews
7.6Boarding
6.8Entertainment
7.3Comfort
8.1Crew
6.8Food
Airline reviews

Booked economy. Seat felt like it was a bit more roomy than my last trans Atlantic flights. I had a nice person sitting next to me. Everything was as good as it could be considering you are 35,000 feet up in the air and in a metal container. Beers, wine, food were all readily available. Plenty of movies and shows to watch. Friendly flight staff

10.0 ExcellentPeter, Mar 2026
IAD - VIE
Read more Austrian Airlines reviews

Booked economy. Seat felt like it was a bit more roomy than my last trans Atlantic flights. I had a nice person sitting next to me. Everything was as good as it could be considering you are 35,000 feet up in the air and in a metal container. Beers, wine, food were all readily available. Plenty of movies and shows to watch. Friendly flight staff

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.

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

Loved the courtesy and punctuality. Very professional and most importantly on time.

Great! They got my vegetarian meal right, flight was comfortable, they helped store my heavy luggage. Pleasant crew and flight staff.

I did wish they would give us the entire little bottle Bailey's instead of just have 1/2 bottle at a time

My layover in Vienna was supposed to be 35 minutes but because my flight was canceled I had to wait in the airport for an additional 8 hours.

The flight was delayed for 30 minutes with no apparent reason. There is no entertainment at all, and no USB or electric outlets for charging your phone or tablet.

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

Stuck on a plane for 6 hours due to a technical or mechanical issue.

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.

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

Very poor. Seats like economy class, food unbeatable, no charging, no entertainment, no WiFi, boarding by bus - no justification for calling and pricing this as business class

The flight itself was pleasant and on time. Crew was very good. However, breakfast food was barely acceptable. Unfortunately this satisfies the recent industry standards. I asked for a sandwich with ham (another choice was cheese), but received a sandwich with roast beef.

had to wait 1 hour once boarded. so we were 1 hour late arriving.

They are absolutely impossible to get hold of. A death in the family caused us to delay our departure. They are impossible to get through to and after waiting 41/2 hours I was told they would not consider helping us. They cancelled our return flight and have not reimbursed anything. I strongly urge readers to consider a different airline.

A lot of snacks and provided on request by traveller. Preferred meals which were on their menu were not always sufficient for those who wanted them. We were told 2 different items and offer which we asked for were not offered initially. We rejected the 3rd item given as a substitute for our initial choices which we didn't want and so we didn't accept it. Eventually our initial choice was offered. During service of coffee and tea, the crew member didn't offer us and moved back. Luckily neither of us wanted tea at that time. Crew members must avoid behavior that may be suggestive of discrimination

The crew was awesome. My husband fell while traveling to the WC and got a head abrasion. The crew helped him greatly and a physician that was also on the flight checked him out as well. They all get an A+!

Online check in and seat assignments are terrible. All 4 flights

Cabin was kept very hot and it was uncomfortable. Entertainment system did not work at my seat. Crew and service is fantastic

Extremely bad BAD BAD BAD. NEVER TURKISH AIRLINES EVER AGAIN..PIRATES COMPANY.

Typically great service from Turkish with comfortable seat and amenitie, good food and great attention from staff.

Delicious food, comfortable and clean plane. It's a little cramped in the hall in front of the gate.

Very hot cabin made long flight uncomfortable, even in business class! Food was great. Istanbul business lounge had great food but too few bathrooms and seating . They also need more electric outlets for charging devices. Appreciate the ability to go through fast track lines w business class

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.

Food was poor quality and the screens for entertainment didn’t work properly

It was a short flight, everything was good with it.

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!

Traveling to a place near Chicago?

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Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago