$354 Find Cheap Flights from Portugal 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 9/19. 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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Cheap Flights from Portugal to Chicago

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

Sat, Dec 5 - Mon, Dec 7
United Airlines Logo
11:20 am - 2:55 pm
LIS
-
ORD
33h 35m
1 stop
United Airlines Logo
10:45 am - 8:10 am
ORD
-
LIS
15h 25m
1 stop
$603United Airlines
Thu, Oct 29 - Mon, Nov 9
Scandinavian Airlines Logo
4:55 pm - 5:45 pm
LIS
-
ORD
29h 50m
1 stop
Scandinavian Airlines Logo
7:15 pm - 4:05 pm
ORD
-
LIS
14h 50m
1 stop
$629Scandinavian Airlines
Mon, Sep 7 - Sun, Sep 20
British Airways Logo
7:10 am - 6:15 pm
LIS
-
ORD
17h 05m
1 stop
British Airways Logo
7:05 pm - 5:45 pm
ORD
-
LIS
16h 40m
1 stop
$667British Airways
Fri, Sep 11 - Mon, Sep 21
British Airways Logo
7:20 am - 6:15 pm
LIS
-
ORD
16h 55m
1 stop
British Airways Logo
5:00 pm - 12:55 pm
ORD
-
LIS
13h 55m
1 stop
$673British Airways
Tue, Jul 21 - Tue, Jul 28
Multiple Airlines Logo
8:25 am - 8:29 pm
OPO
-
ORD
18h 04m
2 stops
Multiple Airlines Logo
7:25 pm - 8:10 am
ORD
-
OPO
30h 45m
3 stops
$771Multiple Airlines
Tue, Jul 21 - Tue, Jul 28
Multiple Airlines Logo
8:25 am - 8:29 pm
OPO
-
ORD
18h 04m
2 stops
Multiple Airlines Logo
7:25 pm - 8:10 am
ORD
-
OPO
30h 45m
3 stops
$777Multiple Airlines
Thu, Nov 5 - Thu, Nov 26
Delta Logo
5:00 am - 6:37 pm
LIS
-
MDW
19h 37m
2 stops
Delta Logo
1:00 pm - 11:20 am
MDW
-
LIS
16h 20m
2 stops
$817Delta
Thu, Oct 15 - Thu, Nov 12
Delta Logo
5:35 am - 6:37 pm
LIS
-
MDW
19h 02m
2 stops
Delta Logo
1:00 pm - 8:00 am
MDW
-
LIS
13h 00m
2 stops
$827Delta
Wed, Dec 2 - Sun, Dec 6
TAP AIR PORTUGAL Logo
6:05 am - 3:30 pm
FAO
-
ORD
15h 25m
1 stop
TAP AIR PORTUGAL Logo
8:10 pm - 3:40 pm
ORD
-
FAO
13h 30m
1 stop
$1,040TAP AIR PORTUGAL
Wed, Dec 2 - Sun, Dec 6
TAP AIR PORTUGAL Logo
6:05 am - 3:30 pm
FAO
-
ORD
15h 25m
1 stop
TAP AIR PORTUGAL Logo
8:10 pm - 3:40 pm
ORD
-
FAO
13h 30m
1 stop
$1,042TAP AIR PORTUGAL
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 Thursday where round-trip tickets can be as cheap as $884. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $1,205 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Chicago, 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 is November, where tickets cost $424 on average for return flights. On the other hand, the most expensive months are March and June, where the average cost of tickets from Portugal is $816 and $679 respectively. For one-way flights, the best month to travel is April with an average price of $343.

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 in the morning, when round-trip flights cost $1,056 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $1,111.

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 $130.

Good to know

Low seasonMarch
Cheapest flight$354
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Lisbon to Chicago

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Chicago is served by 3 major airports. Chicago Midway Airport (9 miles) is the closest to the center of Chicago. Chicago O'Hare Airport is 16 miles from the center and Chicago Greater Rockford is 79 miles away from the center.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $704. The cheapest price found on KAYAK in the last 2 weeks cost $561 and departed from Lisbon Humberto Delgado 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 $641 or less one-way.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airline flying from Portugal 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 Portugal 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.
7.2
TAP AIR PORTUGALOverall score based on 2280 reviews
7.1Comfort
6.2Food
7.0Boarding
6.3Entertainment
7.8Crew
Airline reviews

The crew was excellent. The food was not good. I have taken many international flights and the meal was not good by comparison.

8.0 ExcellentAnonymous, Jun 2026
LIS - NCE
Read more TAP AIR PORTUGAL reviews

The crew was excellent. The food was not good. I have taken many international flights and the meal was not good by comparison.

On both flights, TAP Air Portugal messed up the seating choices that I paid for. They acknowledged that I had purchased seating, that they were errant in ensuring my choices, but told me nothing could be done about it. When I asked to be refunded, I was directed to "talk to someone from Air Portugal" Mon-Friday, and then I was dismissed. No help, no phone number provided to me. I was very annoyed both times and feel cheated.

The worst thing was baggage claim. In my return flight I was waiting 90 minutes for my baggage. and when I asked the airport they said it’s the airline. So frustrating after an 8-hour flight.

Business class seats aren't comfortable. Food was not good.

Didn't make announcements during boarding, flight attendant seemed annoyed when I asked for water. Too many hours between flights. Confusing check in at the Lisbon airport.

Chaotic boarding with no announcements. Carry on luggage needs to be checked. Bare minimum zero frill flights. Not a whole lot of anything positive to be said .

It poured rain, our luggage was sitting out in it uncovered on the transport cart while our plane was delayed! Nice business class plane for short flight to Lisbon, but more delay & rain in Lisbon, with terrible Business class seat with no entertainment & cold food on longer flight to London…ALL LUGGAGE AND CLOTHES INSIDE THEM WERE SOAKED THROUGH!!! Could only try with hair dryer to get some drying before quick turn round to train trip.

Delayed at the beginning and the end and almost missed our connection

Menzies group staff not very sympathetic good at breaking up families during the boarding process

They left our luggage uncovered on tarmac in pouring rain during an hour delay of departure! At our final destination, we found ALL OF OUR CLOTHES/SHOES soaked all the way through!! Our 1st connection plane was a great business class accommodation but only 50 minutes long. Our 2nd connection from Lisbon (another delay with luggage uncovered on tarmac) had only the extra legroom and mediocre food in business class - no entertainment and no extra comfort seating. Will not use TAP Air Portugal again!

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
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
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.