$360 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 11/5. 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

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These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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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, Nov 1 - Mon, Nov 10
Turkish Airlines Logo
9:15 am - 11:05 amSKP-ORD
31h 50m1 stop
Turkish Airlines Logo
11:50 am - 7:45 pmORD-SKP
24h 55m1 stop
$630Turkish Airlines
Find Deal
Sat, Nov 1 - Mon, Nov 10
Turkish Airlines Logo
8:35 pm - 11:05 amSKP-ORD
20h 30m1 stop
Turkish Airlines Logo
8:20 pm - 7:45 pmORD-SKP
16h 25m1 stop
$631Turkish Airlines
Find Deal
Tue, Sep 23 - Sat, Apr 4
LOT Logo
1:35 pm - 7:40 pmSKP-ORD
13h 05m1 stop
LOT Logo
5:10 pm - 4:45 pmORD-SKP
40h 35m2 stops
$632LOT
Find Deal
Sat, Sep 27 - Tue, Apr 14
LOT Logo
5:30 pm - 12:05 pmSKP-ORD
25h 35m1 stop
LOT Logo
9:40 pm - 4:45 pmORD-SKP
12h 05m1 stop
$633LOT
Find Deal
Sat, Sep 27 - Tue, Apr 7
LOT Logo
5:30 pm - 12:05 pmSKP-ORD
25h 35m1 stop
LOT Logo
9:40 pm - 12:55 pmORD-SKP
32h 15m1 stop
$637LOT
Find Deal
Tue, Dec 9 - Tue, Mar 24
Austrian Airlines Logo
4:30 am - 2:00 pmSKP-ORD
16h 30m1 stop
Austrian Airlines Logo
2:24 pm - 11:45 amORD-SKP
15h 21m2 stops
$672Austrian Airlines
Find Deal
Thu, Sep 25 - Sat, Apr 18
United Airlines Logo
4:25 am - 1:20 pmSKP-ORD
15h 55m1 stop
United Airlines Logo
4:20 pm - 11:50 amORD-SKP
12h 30m1 stop
$684United Airlines
Find Deal
Wed, Oct 8 - Fri, Oct 17
Lufthansa Logo
6:15 am - 2:55 pmSKP-ORD
15h 40m1 stop
Lufthansa Logo
3:05 pm - 2:05 pmORD-SKP
16h 00m1 stop
$686Lufthansa
Find Deal
Tue, Sep 30 - Tue, Apr 7
United Airlines Logo
4:25 am - 1:20 pmSKP-ORD
15h 55m1 stop
United Airlines Logo
4:20 pm - 11:50 amORD-SKP
12h 30m1 stop
$687United Airlines
Find Deal
Mon, Sep 22 - Sat, Apr 4
Austrian Airlines Logo
4:25 am - 6:25 pmSKP-ORD
21h 00m2 stops
Austrian Airlines Logo
1:12 pm - 12:15 amORD-SKP
28h 03m2 stops
$692Austrian Airlines
Find Deal

Everything you should know

When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 19% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$630
Typical prices: $562-640
Turkish Airlines
Sat 11/1Mon 11/10
SKP - ORD • 1 stop
Cheapest one-way
$360
Typical prices: $494-581
Multiple Airlines
Wed 11/5
SKP - ORD • 3 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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 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 $585 on average for return flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from North Macedonia is $1,225 and $796 respectively. For one-way flights, the best month to travel is November with an average price of $585.

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 4 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$360
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 5% 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.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as $655. On the other hand, the most expensive day to fly is Wednesday, where round-trip prices are $702 on average.

  • 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.

  • What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

    The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the morning, when round-trip flights cost $655 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally at night, which is peak travel time and where the average cost of a ticket is $734.

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

    Each week there are around 11,595 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

 
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
LOTOverall score based on 1114 reviews
7.0Entertainment
7.6Boarding
7.5Comfort
7.2Food
8.2Crew
Airline reviews

Boarding was delayed for an unknown reason for more than an hour. While the airplane was at the gate, the boarding time was moved by 10-20 minutes every 15 minutes. No entertainment on the plane.

6.0 GoodMariusz, Sep 2025WAW - KRK
Read more LOT reviews

Boarding was delayed for an unknown reason for more than an hour. While the airplane was at the gate, the boarding time was moved by 10-20 minutes every 15 minutes. No entertainment on the plane.

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.

During the flight, the fleas biting me in the plane.

Agents helping disable person doesnt know connections to Poland and after 9 agents helping and 2hours ,we made it to proper terminal. Polish Dreamliner its Polish nightmare liner with so narrow seats and no room under front seat for bag and feet,in economy class.To upgrade, to higher standart cost an arm and leg ,even there are empty seats No good experience overall

The crew and flight were amazing . However , my bag’s locker got broken and no refund provided . Everything else was amazing except this bad incident that ruined my experience

Bags lost no more to say, bad communication and no urgency to get it back to the hotel by the airline properly the worst airline I have used.

It was was okay but the seat was stiff and hard to sit on it!!

Seats were so uncomfortable, my butt hurts so much, I wish they have more cushions,it really was horrible, Except that, Stewarts were polite food was decent

Plane is super outdated, seats not that comfortable for business class. Lounge also out dated. They need to catch up to 2024. Don’t think I’d ever fly again.

Everything was good, flight was smooth and on time Like service

They had me unpack a handbag 2 lbs overweight into another handbag 8 lbs underweight for a Bible.

My flight was canceled and even though I paid אם KAYAK you didn't even answer me and obviously didn't refund my money. I will never buy a ticket through you again.

One thing I really liked about Austrian Airlines was that the flight attendants were very kind, and the in-flight entertainment offered many choices. One thing that could be improved is the meal service, since only a vegetarian option was offered — it would be better to have at least two choices

One thing I really liked about Austrian Airlines was that the flight attendants were very kind, and the in-flight entertainment offered many choices. One thing that could be improved is the meal service, since only a vegetarian option was offered — it would be better to have at least two choices.

Despite the booked seats in front of the land we were moved to the back of the plane even first like 8 lines were totally without pasangers. When I tried to sit on empty seat flight attendant asked me to go to my dedicated seat in the fully crowded back of the plane. She was not able to explain why. Food was very poor on flight LAX - VIE.

Austrian Airlines help and service was fine, but Kayak misled us into believing we had purchased a Business Class ticket. In fact, the tickets were only upgraded Coach Class tickets with luggage restrictions that belonged to the Coach Class. Very disappointed! Paid over $$$$ 9K for the two tickets. Very disappointing!

Quick and organized boarding process, friendly staff but not as many snacks and drinks as the previous flight overnight

Landing was a little hard. Food was not great My prior review was for the flight to nyc too

Landing was a little hard. Food was not great. No options.

I love this airline.God bless CAO and the whole staff of this company

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

Small seat space for 13 hours flight, they charged for baggage , very bad quality of food,

I was sitting almost in the back, the seats are very tight and there’s no legroom, it’s uncomfortable for a long distance

Absolute worst airline. Charged us $720 to check 4 bags (2 of which were carry-on). Entertainment systems didnt work. And on a 12 hour flight they served 2 meals and never once came around outside of those 2 meals with a beverage or cup of water. Will never fly them again.

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.

Amazing trip! No delays, no broken or lost luggage, and amazing food.

The food we received during the flight was excellent. The service was very friendly. Definitely the best value for the money when flying across the Atlantic.

I use a wheelchair for mobility. Both in my flight from Houston and back to Houston from Istanbul, the Turkish airline staff asked that I claim my wheelchair at the luggage area. On arrival to Istanbul, parts of the wheelchair were in disarray at that time I raised no objection however upon claiming my wheelchair in Houston parts where outright missing. In both occasions, upon arriving in Houston and arriving in Istanbul, I asked multiple times why am made to pick up my wheelchair in the baggage claim rather than at the jet bridge. Getting the wheelchair at the jet bridge minimizes the probability of loosing parts because they can be hopefully reclaimed on the spot. I was told in Houston that a manager turned down my request to claim the wheelchair at the jet bridge in Houston. This is extremely frustrating because a wheelchair is not a set of clean underwear or a toothbrush- this is the way I move. A Turkish Arline staff took my complaint at the luggage claim area in Houston but as of the writing of this review the only contact I have received from the airline is because I initiated a claim rather than her as she told me she would.

The security at the airport was excellent. The one criticism is the boarding process just before entering the plane. There were only 2 boarding lines and there were no barriers thus leading to a mass rush to enter the plane. I suggest that they board by rows, eight or ten rows at a time to prevent the mass rush to enter the plane. Otherwise, I would highly recommend Turkish Airlines

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

I darted through the Frankfurt airport to make my connecting flight. I asked if it was a possibility to upgrade and the agent did. This was the kindest gesture and it made up for the previous delayed flight and distress/anxiety of anticipating that Zi was going to miss my Frankfurt-Chicago connection. I cannot express my gratitude for the upgrade.. I am 5feet 10 inches do the leg space was amazing.

I meant this flight was not good, the one from Tirana to Frankfurt was better!

I was very grateful for Lufthansa's role in organizing mobility support. The touchscreen on my seat was faulty: slow, stained (I couldn't get it clean), and glitchy. This made selecting movies extremely time consuming, and twice I had to start all over from the beginning.

The crew was the best I’ve ever encountered. Business class was spacious, immaculate, and very modern.

I wish seats were not reclinable. It's so claustrophobic when the person in front of you spends most of a nine hour flight leaned all the way back. The crew was really nice though and the dinner (red Thai curry) was pretty compelling.

Our flights were severely delayed, then canceled and we had to fly out next day with no sleep accommodation help. This led to our baggage being lost and the service reps after baggage couldn’t be bothered to help. They kept sending us to different counters when we were at the right counter to begin with. The only saving grace was the angel woman supervisor with blond hair who helped us put in a missing baggage claim.

The boarding system was all bogus - employees at the boarding gate were not sound like proffesional or may be possibly rational

I got an email in the morning of the flight 1/7, from Kayak, that I was rebooked from UA 906 to LH 430. Nobody at Lufthansa ot United knew about this. I went to both counters. at the airport. Also, Cheap Flights, who I booked the ticket through, did not know. I ended up staying on the United flight. But this was very disturbing, since I got a very late notice that I was rebooked to an earlier flight, I hurried to the airport to find out after a lot of inquiring that this was a mistake. Not a good Kayak experience.

After living in Europe for five years and flying with Lufthansa and KLM airlines, I’ve realized that United Airlines is now a budget carrier. The flight attendant are not friendly. The seats are not comfortable. And everything comes at a cost. I will be flying with KLM and Skyteam like Delta to the US going forward no doubt. United Airlines is not what it once was:

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!

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.

I purchased an exit row seat and priority boarding, about 3 months in advance. Without any communication whatsoever, my seat was moved to row 2, when I checked my reservation 2-3 days before departure. As no exit row seats were available anymore, I selected a seat 1C. However, once at the airport, I was issued maybe the worst possible seat, 29E, middle seat, one row before the last. It is not worth my time to request the refund on the ancillary purchase, I am simply done flying with Air Serbia. Also there was no boarding process to speak of at all, or online check in.

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