How much is a ticket from Chicago Midway to Portland?

Depending on when you travel and how far in advance you book, fares between Chicago and Portland can differ a lot.

The lowest fare seen in the past 15 days was $88.

If you’re flexible with timing, consider overnight flights — they often cost less and are less crowded. Exploring multiple date and time combinations can help you find the cheapest solution.

Which airports serve Chicago and Portland?

When planning a trip of about 1747 mi, it's a good idea to check flights from surrounding airports too.

• Airports in Chicago: Chicago is connected to 3 airports - Midway, O'Hare, Rockford.
• Airports in Portland: The only active airport in Portland is Portland.

The closest airport isn’t always the cheapest — it’s worth checking the alternatives too. In some cities, smaller airports offer lower fares than the main ones.

Explore flights from Chicago Midway to Portland your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by agency like eDreams or Expedia. Options include Delta, United, American, and more.

Other popular destinations

Also interested in United States? Check out: Las Vegas, Los Angeles, Miami, New York City, Orlando.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.