Find cheap flights from Chicago to Portland

CHI - PWM

Find cheap flights from Chicago to Portland

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Chicago (CHI)
Portland
Mon 5/10
Mon 5/17
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Good to know

Low season

AugustBest time to beat the crowds with an average 39% drop in price.

High season

DecemberMost popular time to fly with an average 16% increase in price.

Average price round-trip

$371(avg. price over the last 2 weeks)

Good deal round-trip

$267or less

Good deal one-way

$196or less

When to book flights from Chicago to Portland

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $196 or less one-way and $267 or less round-trip.
  • The cheapest flight from Chicago to Portland was found 32 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is August.
  • Morning departure is around 14% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking flights from Chicago to Portland

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Top 4 airlines serving Chicago to Portland

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,236 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "The sanitizing of the aircraft was beyond expectations. The personal wipes were a plus so we could clean the areas around our seats to our satisfaction. The individual snack bags are a great idea to minimize handling."

Pros: "Crew was very rude both to and from Sydney. Always made people feel like they were a burden and they didn’t want to even be there. Will never fly Delta again, especially internationally."
Cons: "Hire employees that at least pretend they enjoy their job."

Pros: "Crew was great, very generous with snacks and beverages, and prior to boarding we were able to switch flights and seats without problem. All the Delta agents were extremely helpful, and had great customer service!"

Pros: "Good crew, kind and hard working staff. It is so nice to have inflight messaging and that was a pleasant surprise that made the flight go quickly."
Cons: "I found the delta app to be less user friendly than the United one. I wish the in flight entertainment were in the Delta app versus downloading yet another app."

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Cons: "Plane was way too hot and stuffy, wasn't until about 20 min into flight before started to cool down."

Cons: "Couldn't believe the flight attendant walked around with a tray of snacks and bananas. When I asked for the banana, she said, "Oh I'm sorry, those are for First Class only". Really?"

Cons: "At least one hour late"

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Pros: "Flight was on time and arrived a little early."
Cons: "I was seated next to a very large man (6’5” he said) and had no room in my seat. Thankfully the seats in front of us were empty and the flight attendant moved him."

Cons: "Ran out of snacks by the time they got to my row"

Pros: "The service was excellent."

Cons: "Boarding was a little bit rushed and the gate agent was visibly irritated by some passengers who didn’t check their bags."

Pros: "As usual great staff and awesome entertainment/connectivity"
Cons: "Due to weather & maintenance flight was delayed for IFR release & fuel temperature gauge issues. Staff was very helpful. Would have appreciated a drink voucher. Some unprofessional passengers took their frustrations out on the flight attendants."

Pros: "Smooth. Fast boarding"

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "It was a very easy boarding process and everybody I can across seemed to be enjoying themselves."
Cons: "Seats were a bit uncomfortable and the entertainment was not readily accessible."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Cons: "Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight."

Pros: "No issues boarding as a group of 6, including one child. We all had at least a personal item and/or a carry-on to stow. The flight was easy, comfortable, and the free movies were current and definitely helped pass the time."
Cons: "We were seated right behind the delta comfort+ and saw the special snacks they got. Being teased by that is not a huge deal, just a little disappointed by the regular snack selection, the snack mix was definitely subpar."

Cons: "I have traveled with my luggage plenty of times through airports and the flight from washington to jacksonville, my luggage came back to me cracked and broken. I was surprised that Delta handling was worse than any of the cheaper flights I normally take and will not be checking any baggage with Delta again."

Cons: "Partner site said it was Aeromexico. First flight was delta so different check bag policy for internal flight that cost me $80. Screw you all"

Pros: "The flight is short"
Cons: "Delayed from 930pm to 6am. Didn't tell us till almost midnight. Because of scheduling issues not weather or anything. The check in people had no idea what I was talking about when I tried to check in for my 6am rescheduled flight."

Cons: "The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN."

Pros: "It was on time"
Cons: "Minimum everything"

Pros: "On time departure; good updates by flight deck; luggage arrived unscathed."
Cons: "Once beverage service was complete, flight attendants retreated to the back of the plane. On a 4-hour flight, it would have been nice to have someone come by and ask if we needed anything, such as water, coffee, or juice. Granola bar was good."

Cons: "All was well"

Pros: "We spent 90 min in line to take off on the tarmac. Pilot kept us informed. Crew were very pleasant."

Cons: "*Again, my first choice of main off the menu, in Delta One, had run out. *Not a fan of the Delta One seats."

Cons: "Flight delayed due to weather and mechanical.. nightmare! Still not sure when I'll get to DCA . I was suppose to get in at 9:30 pm. Flight from atlanta won't leave until 10:20 pm."

Cons: "Flight was cancelled and travel delayed by 24 hours."

Pros: "They arrived on schedule."
Cons: "Seated in the rear middle seat. I had no options to select a seat when I checked in or made my reservation that wasn't an extra charge. I'mover 6' tall and middle seats are painful, especially cross country. Airlines need to be a little more attentive to their customers' needs. If a passenger is taller than average, and the flight is more than 60 minutes, provide comfortable seating at no extra charge. If a customer has a short layover, which their system knows about since it is the sourve of the flight plans, put the customer toward the front of the aircraft since these flights are habitually late and customers end up having to sprint through airports to try to make connections."

Cons: "Delays and ground chaos nearly caused us to miss our international connection. Gate staff unable to provide assistance with booking on connecting partner airline. Gate staff unaware of new terminal 3 to TBIT airside shuttle nearly directed us to leave domestic and requeue for international security. Will like skip Delta connectors to long haul international flights and just fly direct from SFO."

Pros: "What I liked: Sky Priority privilege came with separate luggage check-in queues and early boarding"
Cons: "What I disliked: Seats were too small No beverages or snacks offered No USB or power outlets available Three different groups board before Delta Comfort (e.g. those needing more time, travelers with children, first/business class) Didn't see the value compared to a less expensive main cabin ticket"

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "Its the way flying should be. The flight attendants were very pleasant and funny"
Cons: "Entertainment system wasn't working all the time. Didn't bother me I was reading"

Pros: "Service"
Cons: "Long delay"

Pros: "Flight attendants were competent."
Cons: "Air conditioning was extremely noisy."

Cons: "Flight attendants were a little snobby and didn't treat all passengers equally, in my humble opinion (note: I was sitting in 1st class)."

Pros: "I liked getting home"
Cons: "Seat 27F is not a seat. The online system messed up!"

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "Smooth boarding, no delays, quiet easy flight, arrived on time and quick deplaning."

Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Pros: "Just absolutely uneventful and quick."
Cons: "TSA"

Pros: "Quick flight - attendants were nice."
Cons: "It was way too hot like the Ac wasn't working. Walked off the plane sweating."

Pros: "Frequent updates by text and email. Pleasant and helpful agent in DTW . Hotel voucher given because of Gold level. Wyndham convenient"
Cons: "Left over 2 hours late, missed connection. No meal voucher in DTW"

Pros: "It was on time, everyone was professional in terms of their attire and attitude. Clean plane. I loved the fact that we had access to in-flight entertainment on even this short flight, and it is always nice that Delta provides a complimentary beverage and pretzels."

Pros: "Got my first class seat, smooth ride, early arrival"

Pros: "The flight was great and landed early."

Pros: "Free novies"
Cons: "Food service and better social distancing"

Pros: "Great service"

Pros: "Almost empty in economy"
Cons: "I liked everything"

Pros: "Clean environment of the terminals and the speed of the shuttle."
Cons: "no comment."

Pros: "It took off on time and life was good."

Pros: "Great service!"

Pros: "Everything"

Pros: "The entertainment was amazing"
Cons: "We were delayed multiple times and landed extremely late"

Pros: "Very affordable! Traveling can be difficult, especially from Chicago O'hare - one of the busiest airports in the country - but everything was made easy for me and was a breeze!"
Cons: "No complaints here!"

Cons: "Requested for wheelchair assistance but none provided?!!"

Pros: "Almost always on time, captain keeps us updated, friendly airline staff"
Cons: "Nothing"

Pros: "On time"

Pros: "Everyone was polite, helpful, and courteous."

Pros: "There were too many gate changes ."

Pros: "I like that they have complimentary snacks"

Cons: "Delay boarding and then dropped us off at a remote runway and had to wait 45 minutes for a bus to main terminal!"

Pros: "Timing and transit time was excellent"

Pros: "Nothing"
Cons: "4 hora de retraso ni una cortesía empleados bien carnepuercos"

Pros: "Everything."
Cons: "Nothing."

Pros: "Price space, time"
Cons: "Waiting.. but better to be early than late"

Cons: "Food was horribe and no dedicated tv per seat"

Pros: "Everything was pretty decent.. Best part was the price.. Boarding was good staff was good"
Cons: "Wasn't enough room.. kind of tight.. Couple more inches all around would have been perfect though"

Pros: "Ease of travel"

Pros: "Everything"
Cons: "No dislikes"

Pros: "No complaints"

Pros: "N/A"
Cons: "The flights were delayed multiple times. No communication at your gates. Oh and I think my favorite was changing terminals and gates 5 TIMES within 1 hour at DFW! RIDICULOUS AND UNACCEPTABLE. NEVER AGAIN!"

Pros: "Everybody was nice my ride was comfortable and they treat me with respect"
Cons: "I like everything"

Pros: "On time."

Cons: "1 hour late. And when the pilot made announcements during the movie it would not pause. We missed parts of the movie. It was annoying."

Pros: "very good no problems.."
Cons: "all good thanks much"

Cons: "Always a problem with these guys"

Cons: "Delayed"

Pros: "The ride was smooth the airplane was the food was OK the stewardess were kind"
Cons: "The ride was smooth the airplane was the food was OK the stewardess were kind"

Pros: "Nothing"
Cons: "Constant delays and cancellenations"

Pros: "Smooth, simple and easy process. Over good experience."
Cons: "I got nothing here."

Cons: "Same as above but I missed a whole day with my relatives at the lake :("

Pros: "The movies"
Cons: "Everything else"

Pros: "That I got a soda"
Cons: "Delayed at Ohare by an hour. Sitting on the Tarmac for a half hour in Reagan, waiting for a gate. This was our leg back to DC, after our leg to Chicago four days previously. On that trip I did a review and gave the whole trip a 1 out of 5 stars. That trip was the trip from hell, with delays, waiting on the Tarmac, deplaning, almost cancelled, more waiting on the Tarmac, wheels up in Reagan, wheels down in ORD, and then more Tarmac waiting for a gate. So I was already more than perturbed when this trip had similar outcomes."

Pros: "Love bed it! Would recommend to family/friends"

Pros: "Smooth trip"
Cons: "Delay delay delay on the flights"

Pros: "I loved the entertainment options"
Cons: "I did not like"

Pros: "It was a good nice ride. The employee was nice."

Cons: "No AC or USB charging ports, no individual entertainment screens."

Pros: "Good value"
Cons: "Poor food quality"

Cons: "Horrible delays and many gate changes"

Cons: "I didn't get vegetarian food that I ordered over the phone and I did made sure that it said vegetarian Jain meal on the ticket that I printed. Very disappointed because no point ordering then. I paid $1234 for the trip. And I am traveling because of funeral."

Pros: "Food, entertainment and free checked bag. Can ask for more!"

Cons: "Delayed as well!!!"

Pros: "entertainment and power outlet"

Cons: "Had to check my bag because they ran out of overhead bin space."

Pros: "Efficient"
Cons: "Free wifi"

Pros: "Getting a meal and drink"

Pros: "One attendant did it all. And very well. Impressive."
Cons: "More snack options."

Pros: "The crew was friendly and patient"
Cons: "The seats aren't very comfortable, but it was a short flight"

Pros: "Fast & efficient"
Cons: "Not much"

Pros: "A FUN HAPPY TIME AS THE CHAPS WHO SAT EITHER SIDE OF ME WERE CHATTY AND HUMOROUS - THEY WERE HAPPY THAT COLUMBUS DAY WAS TO BE CELEBRATED THIS PAST MONDAY AND WHEN I TOLD THEM I WAS TO CELEBRATE CANADIAN THANKSGIVING WITH MY SON AND HIS AMERICAN WIFE AND THEIR 2 CHILDREN - WELL LET'S JUST SAY THE 3 HOURS OF THE FLIGHT FLEW BY. SMILE"

Pros: "Flight attendant noticed my husbands t-shirt from Galveston and talked briefly about it. Smooth flight."
Cons: "Since it was a smaller plane the seating room was tight."

Pros: "Our connecting flight was more comfortable than flight from San Francisco"
Cons: "Delay because of change of plane and 3 gate changes"

Cons: "The $25 each way for piece of luggage"

Pros: "nothing"
Cons: "crying babies & no food"

Pros: "Same as above"
Cons: "Same as above"

Pros: "It was on time"
Cons: "Nothing was bad, completely average. Nothing impressive either."

Pros: "The personal tv"
Cons: "Having to pay an extra fee just to watch whatever I wanted"

Pros: "Late boarding, other then that ok."

Pros: "That I arrived to Memphis on time!"
Cons: "That the air isn't on until its time to board, instead of being a lil before its time to board."

Pros: "Same as above"

Cons: "Long waiting to take off other than that good"

Cons: "Arrived at 1:30 AM"

Cons: "N/a"

Cons: "Very long delay"

Pros: "i liked the fact that it was a short trip so i could make my way home from there."

Pros: "On time!!!!"
Cons: "Only water served"

Cons: "The delays"

Cons: "Same as first leg of the trip"

Pros: "coffee was good"
Cons: "Only got to serve it once due to turbulence"

Pros: "I made it to my destination and was offered a beverage"
Cons: "Everything else. No one greeted me. No TVs. Luggage was ruined. Ppl were rude"

Pros: "Was given a couple of blankets that I asked for. Everyone was very professional. Very accommodating."

Cons: "no outlets, no tv, no wifi"

Pros: "Early boarding for passengers with children under age of 2 was super helpful for me as I was traveling by myself with baby for the first time!"

Cons: "Wifi did not work. Limited food & beverage choices."

Pros: "Comfortable"
Cons: "Cat meowing loudly in seat in front of us"

Pros: "I made it alive"

Cons: "Crowded seating."

Pros: "Delayed a lot"

Pros: "Nothing"
Cons: "Everything"

Pros: "Early arrival"
Cons: "No free snacks"

Pros: "Early"

Pros: "Fast and easy yo use"
Cons: "None"

Cons: "Poor seat selection options."

Pros: "On-time flights"

Pros: "On time"

Cons: "Same as the first one"

Cons: "Delays"

Cons: "Weather delay but then sat at the gate for nearly an hour waiting for "fuel". Give me a break! No update as to why we were waiting, just said we would leave in 15 min an hour before we left."

Cons: "Didn't make it"

Cons: "Paid for first class, didn't get offered dinner"

Pros: "I wish I would have caught her name but the staff member at the boarding gate was fabulous! She is someone I would want representing my company."
Cons: "The wafer served with the beverage & my seat assignment stunk."

Pros: "I had no complications before/during this flight. It was as if the air travel angels were smiling down on me, making little decisions like, "Sure. Give her that rare luxury of having no one sitting beside her... twice in a row. And toss in not one, but two of those United Airlines cookies." (Those cookies are sooooo good.) Really, at the moment, I can think of nothing anyone could've done any better."
Cons: "N/A"

Pros: "We got to New York thank god"
Cons: "Delay over 1hour and half"

Cons: "Had to check a bag I've carried on several other times."

Cons: "Check in"

Cons: "Free food and baggage"

Cons: "They don’t care if you have a medical emergency"

Pros: "A great change since Frontier moved to Terminal 5 at O'Hare."

Pros: "Nothing"
Cons: "Delays, gate changes, lack of notification, last minute changes."

Pros: "Arrived 30 min early"

Cons: "We waiting 2hours... delay Something to fixing on plane! I miss good business in Tampa because of that"

Pros: "Nothing"
Cons: "Everything about frontiers"

Cons: "not clean"

Pros: "It was fast"

Pros: "No issues"
Cons: "Everything was fine"

Pros: "a smooth ride. we left a half an hour late."
Cons: "paying the carry on fee"

Pros: "Overall quickness and friendliness of staff."
Cons: "No free food."

Pros: "Very comfortable ride and spacious"

Pros: "Attendants at the boarding site in Phoenix are great!"

Pros: "Bag charged"

Cons: "Terrible information and no service."

Cons: "Short-staffed, so short tempered workers.kiosks did not work. Nickled and dimed on everything. Like flying in prison. No light and a cold hard bench seat. Awful."

Cons: "Look like frontier is always late"

Pros: "Attendants were friendly, plane was clean, and the experience was overall great."
Cons: "It would have been nice if the plane carried wifi or some kind of tv/music option for entertainment."

Pros: "Nothing."
Cons: "Everything."

Pros: "uh the "big front seat" was decent? fairly roomy and still cheap"
Cons: "fuckin screaming children everywhere, it was horrendous"

Cons: "Trip had over 8 hours of delays."

Cons: "no free snack? not even a bag of peanuts?! disappointing"

Cons: "I did not like the long delay"

Cons: "Late late late arrival."

Cons: "delays with NO feedback"

Cons: "there were too many delays and the situation was handled poorly. I do not plan to fly Frontier again in the future."

Cons: "They nickle and dime you to death. They even charge you for soda!"

Pros: "Getting where I was going"
Cons: "Everything else."

Cons: "See above."

Pros: "Nothing"
Cons: "Everything"

Pros: "Very efficient."
Cons: "No free beverage."

Pros: "Politeness"
Cons: "Overall everything"

Cons: "to expensive to cary on a bag."

Pros: "Middle seat was empty"
Cons: "The delay. No food. No apologies"

Pros: "The tate"
Cons: "Paying for bags"

Pros: "I was upgraded for free!"
Cons: "The payment necessary for baggage."

Cons: "Everything!!"

Cons: "Horrible!!! Late doy and I Need to pay for my hand luggage. Never travel with Frontier!"

Pros: "Aircraft"
Cons: "Nothing"

Cons: "Food"

Pros: "They keep it simple, planes are new and clean, and many of my flights have arrived early with Frontier. Great airline, great value, and allows me to see family often and not break the bank! And for the last couple of flights the attendantsame have made the safety demo and announcements comical and therefore bringing attention back to safety demo and off personal electronics."

Cons: "Lots of screaming children, but I had to fly to Orlando."

Pros: "It was very punctual"

Pros: "Very informative on where to go!"
Cons: "Not very informational on security policy"

Pros: "Everything was good, no complaints"

Pros: "Staff"

Cons: "The Chicago airport was terrible both times. Things not clearly marked. Staff not friendly or available. Long term parking very hard to find and pricing very unclear. Didn't realize we would have to pay additional for just a seat and carry on luggage"

Pros: "Cheap..."
Cons: "Delaaaays"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago to Portland

Airlines flying from Chicago to Portland have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago to Portland

Mandatory masks

Masks required on board, masks provided on flights from Chicago to Portland

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Portland

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to Portland

Book cheap flights from Chicago to Portland

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United Airlines
2h 27m
ORD - PWM
6/5
Sat
nonstop
American Airlines
2h 27m
ORD - PWM
7/24
Sat
2 stops
Amtrak
43h 35m
ZUN - OR7
7/24
Sat
2 stops
Amtrak
43h 35m
ZUN - OR7
6/1
Tue
2 stops
Amtrak
43h 35m
ZUN - OR7
5/25
Tue
2 stops
Amtrak
43h 35m
ZUN - OR7
6/24
Thu
2 stops
Amtrak
43h 35m
ZUN - OR7
6/24
Thu
2 stops
Amtrak
43h 35m
ZUN - OR7
7/24
Sat
2 stops
Amtrak
43h 35m
ZUN - OR7
5/22
Sat
2 stops
Amtrak
43h 35m
ZUN - OR7
5/22
Sat
2 stops
Amtrak
43h 35m
ZUN - OR7
5/29
Sat
2 stops
Amtrak
43h 35m
ZUN - OR7
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