$437 Find Cheap Flights from Taiwan 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 5/1. 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

 
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 Taiwan to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Taiwan 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 Taiwan to Chicago

Thu, May 7 - Tue, May 26
Delta Logo
9:50 am - 5:56 pm
TPE
-
MDW
21h 06m
2 stops
Delta Logo
7:13 pm - 7:55 pm
MDW
-
TPE
35h 42m
2 stops
$652Delta
Fri, May 1 - Wed, May 13
United Airlines Logo
2:30 pm - 5:25 am
TPE
-
ORD
27h 55m
1 stop
United Airlines Logo
10:00 am - 4:05 am
ORD
-
TPE
29h 05m
2 stops
$652United Airlines
Fri, May 1 - Fri, May 8
United Airlines Logo
2:30 pm - 12:59 am
TPE
-
ORD
23h 29m
1 stop
United Airlines Logo
7:40 am - 6:45 pm
ORD
-
TPE
22h 05m
1 stop
$654United Airlines
Fri, May 1 - Fri, May 8
Delta Logo
9:35 am - 9:06 am
TPE
-
MDW
36h 31m
2 stops
Delta Logo
6:36 pm - 7:55 pm
MDW
-
TPE
36h 19m
2 stops
$654Delta
Wed, Apr 29 - Wed, May 6
ANA Logo
9:55 am - 8:46 pm
KHH
-
ORD
23h 51m
2 stops
ANA Logo
7:40 am - 9:00 pm
ORD
-
KHH
24h 20m
2 stops
$1,035ANA
Wed, Apr 29 - Wed, May 6
ANA Logo
9:55 am - 2:55 pm
KHH
-
ORD
18h 00m
1 stop
ANA Logo
7:40 am - 9:00 pm
ORD
-
KHH
24h 20m
2 stops
$1,110ANA
Thu, Apr 23 - Sun, Apr 26
Cathay Pacific Logo
11:40 am - 1:55 pm
KHH
-
ORD
39h 15m
1 stop
Cathay Pacific Logo
4:15 pm - 10:10 am
ORD
-
KHH
28h 55m
1 stop
$1,168Cathay Pacific
Thu, Apr 23 - Sun, Apr 26
Cathay Pacific Logo
1:40 pm - 1:55 pm
KHH
-
ORD
37h 15m
1 stop
Cathay Pacific Logo
4:15 pm - 12:40 pm
ORD
-
KHH
31h 25m
1 stop
$1,172Cathay Pacific
Tue, Apr 7 - Thu, Apr 16
Japan Airlines Logo
2:20 pm - 7:20 am
TSA
-
ORD
30h 00m
1 stop
Japan Airlines Logo
2:10 pm - 11:15 am
ORD
-
TSA
32h 05m
1 stop
$1,287Japan Airlines
Mon, Apr 27 - Fri, May 1
Japan Airlines Logo
9:40 am - 8:12 pm
TSA
-
ORD
23h 32m
2 stops
Japan Airlines Logo
2:30 pm - 11:15 am
ORD
-
TSA
31h 45m
1 stop
$1,338Japan 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 day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as $1,308. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $1,926 on average.

What is the cheapest time of day to fly to Chicago?

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago is generally at night, when round-trip flights cost $1,589 on average. The most expensive time of day to fly to Chicago is generally at night, which is peak travel time and where the average cost of a ticket is $1,589.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Taipei City Taiwan Taoyuan Intl Airport $1,606 round-trip.

How far in advance should I book a flight to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $151.

Good to know

Low seasonFebruary
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 31% lower on average.

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    There are 3 major airports in Chicago. The nearest airport from Chicago city center is Chicago Midway Airport (9 miles), followed by Chicago O'Hare Airport (16 miles) and Chicago Greater Rockford (79 miles).

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $1,418. The cheapest price found on KAYAK in the last 2 weeks cost $1,095 and departed from Taipei City Taiwan Taoyuan 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.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $1,095 or less one-way and $1,606 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top 3 airlines serving from Taiwan 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 Taiwan 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.
7.9
DeltaOverall score based on 8288 reviews
8.1Boarding
7.9Comfort
7.2Food
7.8Entertainment
8.5Crew
Airline reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

10.0 ExcellentDebra, Mar 2026
PBI - ATL
Read more Delta reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

No pilots so we were two hours late taking off and then no gate agents when we arrived in Salt Lake.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

After each meal was served I didn't see any flight attendant offer coffee or tea to the passengers after the initial drinks were offered. Other flights I had been one it was standard procedure to offer hot drinks after the meal service.

It was great. It was my first time with Cathay Pacific and I really recommend.

Selected ovo lacto meal because I’m ok with milk products but not any meat. It was terrible. We had the same selection back in October when we had traveled and it was pretty good at that time. It was gross this time.

I was mid plane and they were already out of the main beef entree....ugh!

Flight delayed first from bad weather, then after boarding there was a problem with the plane. We had to get off and onto another plane...connections were missed and the trip took an additional 10 hours!! Pre-paid seatting was not honored due ro last minute carrier changes. Most of the trip was on Japan Airline.

Vegetarian options should be included with every meal. Even just simple steamed vegetables and whole grains would capture a wide audience.

Cramped, hot and the plane was grubby. Also the plane was an hour late and it took an hour to get my luggage once I got to LAX.

Extensive delays, poor organization to board people, as it felt like chaos to get inside of the plane. No lines, everyone gathering together like a mayhem, very confusing. Passengers out of hand and rude, which is not the airlines fault. However, there should be rules, e.g., not letting one passenger take 2+ spots in the overhead bin.

The bed was alright in business class. Food variety and quality were not up to the mark compared to the business class airfare.

Food , drink experience were great with Cathay. Crew service was excellent. Clean toilet and full snack bars always, pilot took of 26minutes later when boarding at Hong Kong with extra US customs check at gate 9 for US flight, but he managed to arrive only 2 minutes later from flight tracker. Smooth flight .

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
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Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.