CHI - PDX

$153 Find Cheap Flights from Chicago to Portland - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Portland departing on 6/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland.
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Everything you should know

Cheapest round-trip
$309
Typical prices: $427-$244
Southwest
Thu 8/20Sun 8/30
MDW - PDX • 1 stop
Cheapest non-stop
$310
Typical prices: $423-$310
Alaska Airlines
Wed 7/1Wed 7/8
ORD - PDX • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to six inches more legroom on this medium-haul route.
Alaska Premium Class adds priority boarding and legroom; Southwest offers free snacks.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $309 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Alaska Airlines, American Airlines and others. Average duration is 4h 27m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $223 (round-trip)
Shortest trip • 6h 04m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 58% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 55% price drop
Most popular
Good to know
Good to know
+1
+1
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Good to know
+1
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Flight Deals
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Flight Deals

Cheap Flights from Chicago to Portland (CHI-PDX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Portland

Thu, Aug 20 - Sun, Aug 30
Southwest Logo
5:30 am - 10:15 am
MDW
-
PDX
6h 45m
1 stop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$309Southwest
Wed, Jul 1 - Wed, Jul 8
Alaska Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
Alaska Airlines Logo
10:59 pm - 5:00 am
PDX
-
ORD
4h 01mnonstop
$310Alaska Airlines
Tue, Sep 8 - Tue, Sep 15
United Airlines Logo
8:12 pm - 10:52 pm
ORD
-
PDX
4h 40mnonstop
United Airlines Logo
8:25 am - 6:37 pm
PDX
-
ORD
8h 12m
1 stop
$311United Airlines
Thu, Sep 17 - Mon, Sep 21
Southwest Logo
6:15 am - 2:45 pm
MDW
-
PDX
10h 30m
2 stops
Southwest Logo
8:00 am - 5:00 pm
PDX
-
MDW
7h 00m
1 stop
$311Southwest
Fri, Aug 14 - Sun, Aug 23
American Airlines Logo
9:30 pm - 11:59 pm
ORD
-
PDX
4h 29mnonstop
American Airlines Logo
11:34 pm - 5:32 am
PDX
-
ORD
3h 58mnonstop
$312American Airlines
Fri, Aug 21 - Sun, Aug 30
Southwest Logo
8:50 pm - 11:05 pm
MDW
-
PDX
4h 15mnonstop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$312Southwest
Sat, Jun 27 - Tue, Jul 7
Delta Logo
3:55 pm - 8:17 pm
ORD
-
PDX
6h 22m
1 stop
Delta Logo
5:30 am - 1:28 pm
PDX
-
ORD
5h 58m
1 stop
$314Delta
Sat, Jul 11 - Sat, Jul 18
American Airlines Logo
10:15 pm - 12:50 am
ORD
-
PDX
4h 35mnonstop
American Airlines Logo
6:07 am - 12:17 pm
PDX
-
ORD
4h 10mnonstop
$316American Airlines
Sat, Sep 26 - Wed, Sep 30
Frontier Logo
2:46 pm - 4:35 pm
ORD
-
PDX
27h 49m
2 stops
Frontier Logo
3:22 pm - 10:01 am
PDX
-
ORD
16h 39m
1 stop
$317Frontier
Thu, Aug 20 - Sun, Aug 23
Delta Logo
7:00 am - 11:45 am
ORD
-
PDX
6h 45m
1 stop
Delta Logo
6:20 am - 5:40 pm
PDX
-
ORD
9h 20m
1 stop
$318Delta
Booking Insights

KAYAK's insights & trends for Chicago to Portland flights

Get data-powered insights and trends into flights from Chicago to Portland to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Portland?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Portland departing in August.

What is the cheapest Chicago to Portland flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The absolute cheapest return flight from Chicago to Portland costs $305 on the route between Chicago O'Hare Intl Airport (ORD) and Portland (PDX). However, over the past month, flights between Chicago Midway Airport (MDW) and Portland (PDX) were, on average, 1% cheaper than other Chicago-Portland routes. The most popular route is between Chicago O'Hare Intl Airport (ORD) and Portland (PDX).

What’s the cheapest day of the week to fly from Chicago to Portland?

The average price of all round-trip flights from Chicago to Portland clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Portland, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Portland, Wednesday is the cheapest day to fly and Monday is the most expensive.

What is the cheapest month to fly from Chicago to Portland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Portland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Portland is August, where tickets cost $94 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $696 and $512 respectively.

Can I save money by flying with a layover from Chicago to Portland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $363, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago to Portland?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Portland, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Portland, you should book around 4 weeks before departure, which saves you about 58% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Portland

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on Alaska Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Gabriel Leigh

Gabriel Leigh

Expert on PDX

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Good to know

Low seasonFebruary
Cheapest flight$153
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago O'Hare Airport to Portland

When to book flights from Chicago to Portland

Are your dates flexible? Find out the best times to travel from Chicago to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Portland

  • Can I fly out of Chicago with pets?

    Traveling with your pet out of Chicago is a breeze as both O’Hare International Airport and Midway International Airport are pet friendly. The pet relief stations in O’Hare International Airport are located at Terminals 1, 2, 3, 5, and the Multi-Modal Facility. Midway International Airport also has pet relief stations located both outside and inside the terminal. The pet relief station located inside the terminal is just past the Concourse A security checkpoint and features artificial turf and an automatic flushing system for easy cleanup.

  • Which airport is best for people with disability needs?

    If you may require accessibility services, you should consider flying out of Midway International Airport. The airport is less crowded than O’Hare International Airport, meaning that most areas and facilities will be available for use. The airport also provides a multitude of accessibility features, such as wheelchair-accessible restrooms and elevators with raised numerals and Braille. The airport also provides parking spots for people with disabilities, which are wide enough for ramp and lift access.

  • How do I get from Portland International Airport to downtown Portland?

    The easiest and most convenient way to get from Portland International Airport to downtown Portland is by using the Max Light rail Red Line, which will take you less than 40min. The last train leaves the airport at 11:50 pm. You can also decide to use private means, such as taxicabs, ridesharing services, or car rental from any of the several car rental companies that operate from within the airport.

  • How do I get from downtown Chicago to O’Hare International Airport?

    Getting to O’Hare International Airport from downtown Chicago is made easy by the city’s intricate public transportation system. You can conveniently use the CTA L Trains to get from the city to the airport, as well as the airport shuttle services that transport passengers to the airport. Additionally, the airport has multiple parking options that allow you to drive to the airport and leave your vehicle for either a short or a long time.

  • What is the cheapest flight from Chicago to Portland?

    In the last 5 days, the lowest price for a flight from Chicago to Portland was $153 for a one-way ticket and $309 for a round-trip.

  • Do I need a passport to fly between Chicago and Portland?

    No, a passport isn't needed to fly from Chicago to Portland. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to Portland?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Portland (Portland). The cheapest flights are generally found on the Chicago O'Hare Airport to Portland flight route.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Portland?

    American Airlines, Alaska Airlines, JetBlue, and Hawaiian Airlines offer inflight Wi-Fi service on the Chicago to Portland flight route.

  • Which aircraft models fly most regularly from Chicago to Portland?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Portland flight route.

  • Which airline alliances offer flights from Chicago to Portland?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Portland, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Portland?

    There are nonstop flights from Chicago to Portland on a daily basis.

  • Which is the best airline for flights from Chicago to Portland, Alaska Airlines or Southwest?

    The two airlines most popular with KAYAK users for flights from Chicago to Portland are Alaska Airlines and Southwest. With an average price for the route of $306 and an overall rating of 7.9, Alaska Airlines is the most popular choice. Southwest is also a great choice for the route, with an average price of $315 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Portland

  • Looking for a cheap flight? 25% of our users found flights on this route for $172 or less one-way and $326 or less round-trip.
  • When traveling out of Chicago, you have the option of departing from any of the two major international airports serving the city: O’Hare International Airport (ORD) or Midway International Airport (MDW).
  • If you have an early flight from Chicago to Portland, consider departing from O’Hare International Airport as the airport has a hotel on its premises where you can book a stay for the night to allow you to be on time for your early morning flight.
  • If you need to get some work done or relax after your flight into Portland International Airport (PDX), make use of the several lounges available at the airport. These lounges are located inside security at Concourse C, D, and E, while there is one lounge located outside security at the Main Terminal.
  • Midway International Airport as the airport provides lactation pods where mothers can breastfeed or pump in a private and safe space. You can find the lactation pod at Concourse A, next to Gate A5.
  • If you misplace any of your items when traveling out of O’Hare International Airport, make sure to contact the organization closest to where you last saw the items. You can contact any of the following agencies: Parking Facilities, food service, TSA Checkpoints, On the Airport Transit Systems, or the Customs Area.

Prefer to fly direct from Chicago to Portland?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Portland.
Find which airlines fly direct from Chicago to Portland Airport, which days they fly and book direct flights.

Direct departures

Chicago to Portland

Monday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Tuesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Wednesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Thursday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Friday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Saturday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Sunday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

See more direct flights

Direct returns

Portland to Chicago

Monday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Tuesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Wednesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Thursday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Friday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Saturday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Sunday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

See more direct flights

Reviews of the top 5 airlines serving from Chicago to Portland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Portland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Alaska AirlinesOverall score based on 12482 reviews
8.1Boarding
7.0Entertainment
7.8Comfort
7.0Food
8.5Crew
Airline reviews

Nice to get moved from a middle seat to an aisle seat upon request, but why wasn’t I put in an aisle seat to begin with? The flight was not full.

8.0 ExcellentDane, May 2026
BOS - PDX
Read more Alaska Airlines reviews

Nice to get moved from a middle seat to an aisle seat upon request, but why wasn’t I put in an aisle seat to begin with? The flight was not full.

They called me 2 hours before my original flight from SFO was to depart to let me know it was delayed and that I would miss my connection. They then rebooked on a different flight leaving a half hour earlier to a different connecting airport, so that I would not miss my connection. It all worked out and I arrived at my destination without a problem and 15 minutes earlier than the original flight would have. Nice!

Couldn’t order food for the family because all the good food was unavailable. We opted for bringing something on with us. I also didn’t like that I had to have T-mobile for online movies. Stupid.

Alaska is by far the best airline to fly with 😍

The flight crew home was so, so friendly and HILARIOUS. I’ll keep flying Alaska like I have for the last 30+ years!

Deboarding the plane was chaos. The passengers in the back of the plane started deplaning before the passengers in the middle of the plane could even retrieve their overhead bags. The staff of the plane did nothing to help.

Enforce the one bag rule for carry ons. Don't allow people to have 2 and 3 carry ons. Make baggage gets loaded onto the correct plane. My bag didn't get put onto my last flight so I didn't get it until the next day.

onboard snack was pretzels, but the FA was super nice when my neighbor asked for cookies instead and also brought some for me. :)

On time. .breakfast was especially good. First class service was special

Had to buy a snack box as I am gluten free. They should be free in extra comfort. Food they provided was awful. Not enough water stops.

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

Everything you need to know for your flight from Chicago to Portland

Information on your arrival and departure airports