#1
Best Places to Meet Halfway Between Chicago and Madrid
Best overall match
Lisbon, Portugal
Best overall balance of travel time, flight price, weather, hotel cost and flight availability.
✈ Chicago 8h 20m
✈ Madrid 1h
From €1068 combined
The Best Meeting Point for Chicago and Madrid: Lisbon, Portugal
28 destinations can be reached directly from both Chicago and Madrid on the same outbound and return dates. Lisbon, Portugal is our best overall match, while Toronto, Canada has the shortest travel time, Boston, United States has the cheapest flights, Guadalajara, Mexico has the best weather, Guadalajara, Mexico has the lowest hotel costs, and Abu Dhabi, United Arab Emirates offers the most matching flight options . You can also search all 28 matching destinations with our destination finder .
Best by Category
Shortest travel time
Toronto, Canada
1h 20m from Chicago ·
7h 40m from Madrid
Cheapest flights
Boston, United States
From €769 combined
Best weather
Guadalajara, Mexico
23°C
Cheapest hotels
Guadalajara, Mexico
€30/night
Most flight options
Abu Dhabi, United Arab Emirates
588 matching trips
Best Overall
Updated
Ranked by travel time, price, weather, hotel cost & availability
Data refreshed within the last 6 hours
#2
Atlanta, United States
#3
Toronto, Canada
Find the Fairest Place to Meet
MeetOnArrival compares live flight prices, schedules and weather forecasts from both Chicago and Madrid to suggest destinations that work for everyone. Open the finder to filter by budget, trip length, and travel dates.
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#4
Boston, United States
#5
Montreal, Canada
#6
Philadelphia, United States
#7
Charlotte, United States
#8
Orlando, United States
#9
Guadalajara, Mexico
#10
San Juan, United States
#11
Dallas, United States
#12
Paris, France
#13
Vienna, Austria
#14
Warsaw, Poland
#15
Amman, Jordan
#16
San Francisco, United States
#17
London, United Kingdom
#18
Dublin, Ireland
#19
Edinburgh, United Kingdom
#20
Zurich, Switzerland
#21
Copenhagen, Denmark
#22
Frankfurt, Germany
#23
Helsinki, Finland
#24
Brussels, Belgium
#25
Amsterdam, Netherlands
#26
Abu Dhabi, United Arab Emirates
#27
Munich, Germany
#28
Tokyo, Japan
Frequently Asked Questions
Why direct flights from both cities instead of a geographic midpoint?
A map midpoint between Chicago and Madrid is usually a town neither of you can reach easily. We instead show real destinations both cities fly to directly, which is normally faster and cheaper than meeting at the literal halfway point.
Where can someone from Chicago and someone from Madrid meet halfway?
Any destination on this page works as a meet-in-the-middle point: both Chicago and Madrid have a direct flight to it, so you arrive in the same place without changing planes. Open the finder to see every shared date, sorted by weather and combined flight cost.
How are the destinations ranked?
Each shared destination is scored on the weather forecast across the trip and the combined flight value from both cities. The finder lets you re-rank and filter by budget, trip length and travel dates.
We live in different countries. Where should we meet between Chicago and Madrid?
Every option here is reachable on a direct flight from both Chicago and Madrid, including international routes, so a cross-border meet-up needs no connections on either side.
Can we search from Madrid and Chicago instead?
The order does not matter. Chicago to Madrid and Madrid to Chicago produce the same destinations, since a direct route works both ways.