Cheap Flights from Madrid to Chicago from $363

Frequently Asked Questions

• What are the cheapest flights from Madrid to Chicago (MAD-CHI)?

  Based on Trip.com data, TAP Air Portugal offers one-way fares as low as $363 on Cheapest nonstop routes (e.g. MAD to ORD on Sun, Nov 1), while TAP Air Portugal offers Cheapest nonstop round-trips from $463 departing on Fri, Sep 11 and returning on Sun, Sep 13.

• Which airlines offer direct flights from Madrid to Chicago?

  At the moment, you can catch a nonstop flight from Madrid to Chicago with the following airlines, including: American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long does it take to fly from Madrid (MAD) to Chicago (CHI) and what is the distance?

  It takes around 9 hours 34 minutes to fly from Madrid (MAD) to Chicago (CHI).

• When is the best time to book flights from Madrid to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Madrid to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there per week from Madrid to Chicago?

  Based on Trip.com data in the past 4 weeks, there is 13 flight per week flying from Madrid to Chicago. You can check the weekly schedule for popular airlines on this route below: American Airlines: S/M/T/W/T/F/S -- AA8666 (12:19)

• How can I find the best deals on flights from Madrid to Chicago?

  To find best deals on flights from Madrid to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sun, Nov 1, with one-way flights priced at just $363.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is American Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Madrid (MAD) to Chicago (CHI) the cheapest?

  The cheapest months to fly from Madrid to Chicago is September, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Madrid to Chicago on?

  After crunching the numbers on our September flight calendar, it's currently cheapest to fly from Madrid to Chicago on September 10, 2026 with avianca, with prices starting at $366.

• Which airports can I fly into Chicago from Madrid?

  You can arrive at any of the following airports in Chicago: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW), and Chicago Rockford International Airport (RFD). Flights from Madrid Barajas Airport to O'Hare International Airport (MAD-ORD) are by far the most popular option for this route.

• Is there any time difference between Madrid and Chicago?

  The time difference between Chicago and Madrid is 7h.

• How do I change or cancel my ticket from Madrid to Chicago?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

• What is the average cost of a one-way flight from Madrid to Chicago?

  Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Madrid to Chicago is $892. Fares vary by travel date, airline and availability.

• What is the average cost of a round-trip flight from Madrid to Chicago?

  Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Madrid to Chicago is $1,277. The final price depends on the outbound and return dates, airline and fare conditions.

• How do I book flights from Madrid to Chicago on Trip.com?

  Enter Madrid and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.

• Are there budget airlines on the Madrid to Chicago route?

  WestJetare the most popular budget airlines flying from Madrid to Chicago. Check baggage, seat and payment fees before comparing the final price.