#1
Best Places to Meet Halfway Between Chicago and Portland
Best overall match
Las Vegas, United States
Best overall balance of travel time, flight price, weather, hotel cost and flight availability.
✈ Chicago 3h 20m
✈ Portland 1h 40m
From €384 combined
The Best Meeting Point for Chicago and Portland: Las Vegas, United States
34 destinations can be reached directly from both Chicago and Portland on the same outbound and return dates. Las Vegas, United States is our best overall match, while Detroit, United States has the shortest travel time, Denver, United States has the cheapest flights, Guadalajara, Mexico has the best weather, Guadalajara, Mexico has the lowest hotel costs, and Santa Ana, United States offers the most matching flight options . You can also search all 34 matching destinations with our destination finder .
Best by Category
Shortest travel time
Detroit, United States
0h 40m from Chicago ·
4h 20m from Portland
Cheapest flights
Denver, United States
From €229 combined
Best weather
Guadalajara, Mexico
23°C
Cheapest hotels
Guadalajara, Mexico
€30/night
Most flight options
Santa Ana, United States
1038 matching trips
Best Overall
Updated
Ranked by travel time, price, weather, hotel cost & availability
Data refreshed within the last 6 hours
#2
Detroit, United States
#3
Washington, United States
Find the Fairest Place to Meet
MeetOnArrival compares live flight prices, schedules and weather forecasts from both Chicago and Portland to suggest destinations that work for everyone. Open the finder to filter by budget, trip length, and travel dates.
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#4
Nashville, United States
#5
Atlanta, United States
#6
Pittsburgh, United States
#7
San Jose, United States
#8
Santa Ana, United States
#9
Reno, United States
#10
Phoenix, United States
#11
Baltimore, United States
#12
Sacramento, United States
#13
Guadalajara, Mexico
#14
Palm Springs, United States
#15
Salt Lake City, United States
#16
Seattle, United States
#17
Albuquerque, United States
#18
Philadelphia, United States
#19
Minneapolis, United States
#20
Austin, United States
#21
Charlotte, United States
#22
Dallas, United States
#23
Norfolk, United States
#24
Charleston, United States
#25
Denver, United States
#26
Orlando, United States
#27
Calgary, Canada
#28
San Francisco, United States
#29
San Jose del Cabo, Mexico
#30
Boston, United States
Frequently Asked Questions
Why direct flights from both cities instead of a geographic midpoint?
A map midpoint between Chicago and Portland 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 Portland meet halfway?
Any destination on this page works as a meet-in-the-middle point: both Chicago and Portland 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 Portland?
Every option here is reachable on a direct flight from both Chicago and Portland, including international routes, so a cross-border meet-up needs no connections on either side.
Can we search from Portland and Chicago instead?
The order does not matter. Chicago to Portland and Portland to Chicago produce the same destinations, since a direct route works both ways.