Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago Midway Airport to Portland
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Delta flights from Chicago Midway Airport to Portland, Maine
Our best Delta deals on Chicago Midway Airport to Portland, Maine flight tickets
Southwest flights from Chicago Midway Airport to Portland, Maine
Our best Southwest deals on Chicago Midway Airport to Portland, Maine flight tickets
See travel insights to Portland from
How to get the cheapest flight ticket from Chicago Midway Airport to Portland, Maine
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest day to depart on your flight to Portland, Maine?
On average, the least expensive day to fly to Portland, Maine from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $193. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $395.
What is the cheapest time of day to depart on your flight to Portland, Maine?
In the afternoon is the cheapest time of day to fly from Chicago Midway Airport to Portland, Maine when you can find flight prices for as low as $210. Flying to Portland, Maine in the afternoon is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $382. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Chicago Midway to Portland flight route?
Fly from Chicago Midway to Portland for the best Chicago Midway - Portland flight prices
What cabin class options are available on Chicago Midway to Portland flights?
There are 1 cabin classes available to choose from on Chicago Midway to Portland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago Midway to Portland?
Southwest, Delta, and Frontier are the most popular carriers operating from Chicago Midway to Portland
What airlines fly to Portland, Maine?
Southwest, Delta and United Airlines are the top three most popular airlines that fly to Portland, Maine from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 87% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 4 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.
When to book flights from Chicago Midway Airport to Portland, Maine
Cheap Chicago Midway Airport to Portland, Maine (MDW to PWM) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Portland, Maine
Best Price Found | $105 |
|---|---|
Fastest flight time | 2h 10m |
Direct flights | Every day |
Airports in Portland, Maine | 1 airport |
How far is Chicago Midway to Portland by plane?
The straight-line distance from Chicago Midway to Portland is 894.8 mi. By plane, this route typically takes 2h 10m.
When did momondo last update prices for flights from Chicago Midway Airport to Portland Airport?
Prices for flights from Chicago Midway Airport to Portland Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Portland Airport?
As of May 2025, there is 1 operator available to choose from for flights from Chicago Midway Airport to Portland Airport.
How old do you have to be to fly from Chicago Midway Airport to Portland Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The necessary travel and health documents for your Portland Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Portland, Maine?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Portland, Maine is Boeing 737-700 (18.25% of total bookings). The next most popular plane models are Embraer 175 (18.25%), Boeing 737-800 (13.14%), and Embraer 175 (Enhanced Winglets) (12.41%).
What is the most popular airline from Chicago Midway Airport to Portland, Maine?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Portland, Maine is Southwest, representing 100% of all bookings.
Best airlines flying from Chicago Midway Airport to Portland, Maine
Compare and see reviews for airlines that fly from Chicago Midway Airport to Portland, Maine with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $191 | Free Cancellation | Rating 8.0 4,293 reviews |
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Portland?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Portland. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to Portland with flexible booking policies on momondo?
momondo does allow users to show only those flights to Portland from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Portland?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Portland from Chicago.
I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to Portland flights. All you need is a valid email address and we will do the rest; it is that quick and easy.