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Cheap Flights from Chicago (MDW) to Madrid (MAD)

Compare Chicago Midway to Madrid flight deals

Find the cheapest month or even day of the year to fly to Madrid

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Flight deals from Chicago Midway to Madrid

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Madrid Airport? If you want to travel next month, return fares start from $1,487. Find the lowest prices on one-way and return tickets right here.
Madrid.$1,023 per passenger.Departing Fri, 11 Dec, returning Sat, 16 Jan.Return flight with KLM and Air France.Outbound indirect flight with KLM, departs from Chicago Midway on Fri, 11 Dec, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Sat, 16 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $1,023, select.
Madrid.$1,027 per passenger.Departing Fri, 18 Sep, returning Tue, 22 Sep.Return flight with Air France.Outbound indirect flight with Air France, departs from Chicago Midway on Fri, 18 Sep, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Tue, 22 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $1,027, select.
Madrid.$1,027 per passenger.Departing Mon, 19 Oct, returning Tue, 27 Oct.Return flight with Air France.Outbound indirect flight with Air France, departs from Chicago Midway on Mon, 19 Oct, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Tue, 27 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $1,027, select.
Madrid.$1,032 per passenger.Departing Sun, 27 Sep, returning Tue, 27 Oct.Return flight with Air France.Outbound indirect flight with Air France, departs from Chicago Midway on Sun, 27 Sep, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Tue, 27 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $1,032, select.
Madrid.$1,032 per passenger.Departing Sun, 1 Nov, returning Fri, 6 Nov.Return flight with Air France.Outbound indirect flight with Air France, departs from Chicago Midway on Sun, 1 Nov, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Fri, 6 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $1,032, select.
Madrid.$1,035 per passenger.Departing Mon, 11 Jan, returning Fri, 15 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 11 Jan, arriving in Madrid.Inbound indirect flight with Delta, departs from Madrid on Fri, 15 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $1,035, select.
Madrid.$1,036 per passenger.Departing Tue, 27 Oct, returning Fri, 6 Nov.Return flight with KLM and Air France.Outbound indirect flight with KLM, departs from Chicago Midway on Tue, 27 Oct, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Fri, 6 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $1,036, select.
Madrid.$1,037 per passenger.Departing Mon, 8 Feb, returning Mon, 15 Feb.Return flight with KLM and Air France.Outbound indirect flight with KLM, departs from Chicago Midway on Mon, 8 Feb, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Mon, 15 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $1,037, select.
Madrid.$1,040 per passenger.Departing Mon, 7 Dec, returning Mon, 14 Dec.Return flight with KLM and Air France.Outbound indirect flight with KLM, departs from Chicago Midway on Mon, 7 Dec, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Mon, 14 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $1,040, select.
Madrid.$1,040 per passenger.Departing Wed, 17 Mar, returning Wed, 31 Mar.Return flight with KLM and Air France.Outbound indirect flight with KLM, departs from Chicago Midway on Wed, 17 Mar, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Wed, 31 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $1,040, select.
Madrid.$1,042 per passenger.Departing Sat, 1 May, returning Mon, 10 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 1 May, arriving in Madrid.Inbound indirect flight with Delta, departs from Madrid on Mon, 10 May, arriving in Chicago Midway.Price includes taxes and charges.From $1,042, select.
Madrid.$1,042 per passenger.Departing Fri, 9 Apr, returning Wed, 28 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 9 Apr, arriving in Madrid.Inbound indirect flight with Delta, departs from Madrid on Wed, 28 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $1,042, select.
Madrid.$1,043 per passenger.Departing Mon, 11 Jan, returning Wed, 10 Mar.Return flight with KLM and Air France.Outbound indirect flight with KLM, departs from Chicago Midway on Mon, 11 Jan, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Wed, 10 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $1,043, select.
Madrid.$1,043 per passenger.Departing Wed, 24 Feb, returning Wed, 17 Mar.Return flight with KLM and Air France.Outbound indirect flight with KLM, departs from Chicago Midway on Wed, 24 Feb, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Wed, 17 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $1,043, select.
Madrid.$1,044 per passenger.Departing Wed, 9 Dec, returning Tue, 9 Mar.Return flight with KLM and Air France.Outbound indirect flight with KLM, departs from Chicago Midway on Wed, 9 Dec, arriving in Madrid.Inbound indirect flight with Air France, departs from Madrid on Tue, 9 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $1,044, select.
Madrid.$1,049 per passenger.Departing Wed, 21 Apr, returning Thu, 6 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 21 Apr, arriving in Madrid.Inbound indirect flight with Delta, departs from Madrid on Thu, 6 May, arriving in Chicago Midway.Price includes taxes and charges.From $1,049, select.

Find the cheapest month to fly from Chicago Midway to Madrid

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Madrid flights are currently cheapest in September.
Jun
Find prices
Jul
from $1,487
Aug
from $1,079
Sep
from $1,027
Oct
from $1,027
Nov
from $1,032
Dec
from $1,040
Jan
from $1,035
Feb
from $1,037
Mar
from $1,040
Apr
from $1,042
May
from $1,042

Chicago Midway to Madrid: Alternative routes

Compare routes from Chicago Midway to Madrid below. You may find an airport to fly into that's cheaper, faster, or easier than Madrid.

Madrid

12km from central Madrid
ClosestCheapest
from $1,023
Search flights

Chicago to Madrid: Flight information

The things to know before you go.
Cheapest flight found$1,023
Cheapest month to flyDecember

Finding cheap flights from Chicago Midway to Madrid: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Madrid is $1,023. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago Midway to Madrid. But we found flights with one or more stops from $1,023.
As of June 2026, there are no flights flying from Chicago Midway to Madrid.
The cheapest month to fly from Chicago Midway to Madrid is usually December.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Madrid Airport on Friday, 11 December 2026.
No airlines currently offer direct flights between Chicago Midway Airport and Madrid Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Madrid but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Madrid is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, KLM offers the cheapest flight tickets to Madrid.

Travelling from Chicago Midway Airport (MDW) to Madrid Airport (MAD): what you need to know

  • Madrid is seven hours ahead of Chicago and is in the UTC+1 timezone.

  • To ensure you get on your MDW to MAD flight, allow plenty of time for things like check-in and baggage drop. Arriving two hours before international departures and one hour before domestic flights is the standard rule.

  • Flying during a peak time like July? Major public holidays and other high seasons can lead to longer lines and delays at security. Be extra cautious and get there up to four hours ahead of an international flight and two hours before a domestic departure.

  • Think about adding a stopover when booking your ticket from Chicago Midway Airport to Madrid Airport. Just uncheck 'Direct flights only' to break up your trip, or maybe even explore a new city along the way. Here's where you can stop between MDW and MAD:

    • Atlanta Hartsfield-Jackson Airport

    • Boston Logan International Airport

    • Philadelphia International Airport

How to find the cheapest flights from Chicago Midway Airport (MDW) to Madrid Airport (MAD)

  • $472 is currently the lowest price for a one-way Chicago Midway Airport to Madrid Airport flight. A return flight starts from $1,023. These prices may change depending on availability.

  • Don't leave things to the last minute. You're more likely to find cheap tickets from MDW to MAD if you book early. Airlines often have some excellent early bird discounts.

  • Getting cheap flights from Chicago Midway Airport to Madrid Airport is easier if you can be flexible with your dates. Use the 'Whole month' search function to see the best prices throughout the month and land a great deal.

  • Getting your hands on cheap flights from MDW to MAD is a cinch with Price Alerts. Simply create one of these automatic alerts and we'll notify you when there's a better deal.

  • Choose your ideal departure and arrival times, airlines and number of stops with the filters. Or sort your results by 'Cheapest' to get the best deals on flights from Chicago Midway Airport to Madrid Airport.

Handy information about Chicago Midway Airport (MDW)

  • You'll find MDW at 5700 South Cicero.

  • When it comes to the on-time performance of Chicago Midway Airport, 76% of flights arrive within the expected timeframe.

  • Central Chicago to Chicago Midway Airport is approximately 16 kilometres. Depending on traffic, it'll take about 25 minutes to get there if you're driving, catching a taxi or ride-sharing.

  • Expect a trip time of around 30 minutes on public transport.

  • Need a handy hotel near MDW? If you've booked an early flight from Chicago Midway Airport to Madrid Airport, these stays will have you moments from your departure lounge:

Arriving at Madrid Airport (MAD)

  • The last thing you want is a long journey to your hotel if you're getting in late on a Chicago Midway Airport to Madrid Airport flight. Check in to one of these accommodation options near MAD instead:

  • Hit the road running by picking up a Madrid Airport rental car. Grab a set of wheels from Record Go, Goldcar or Click and Rent to explore Madrid and beyond.

  • Lock in the best possible rate by booking your ride from Madrid Airport around one week ahead of your trip.

Getting from Madrid Airport (MAD) to central Madrid

  • From Madrid Airport, Madrid is approximately 13 kilometres away. It takes around 20 minutes to drive to the centre.

  • It'll take around 30 minutes when travelling by public transport.

When to fly to Madrid Airport (MAD)

  • It's time to choose your trip dates for your flight from Chicago Midway Airport to Madrid Airport. July is the busiest month to visit Madrid. If you want a more relaxed vibe, go in March.

  • Book your flight from Chicago Midway Airport to Madrid Airport for July if you'd like to explore Madrid during its warmest month. Expect temperatures of between 18ºC (64ºF) and 37ºC (99ºF).

  • January sees average temperatures of between 0ºC (32ºF) and 12ºC (54ºF). Look for cheap tickets from MDW to MAD sometime around then if you like cooler conditions.

Explore more of Spain

  • Madrid is always a good idea, but there are so many other corners of Spain you should also see. Around 274 kilometres north-east of Madrid, a trip to Zaragoza will fill your itinerary to the brim. Start with leading attractions like Plaza del Pilar, La Seo del Salvador and Basílica de Nuestra Senora del Pilar.

  • Around 177 kilometres west of Madrid, Salamanca is another essential stop in Spain. Get a taste of what this destination has to offer at Catedral de Salamanca, Salamanca, Casco Historico and Plaza Mayor.

Plan the rest of your trip from Chicago to Madrid

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.