Find Cheap Flights from Oregon to Chicago

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Book cheap flights from Oregon to Chicago (round-trip)

Airports
Origin
Portland
$138
only
$138
Eugene
$346
only
$346
Medford
$363
only
$363
Destination
Chicago
$138
only
$138
$264
only
$264
Tue, Mar 6
PDX
ORD
6h 39m
Tue, May 1
ORD
PDX
4h 20m
Trip: 56 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

PDX
ORD
Good 6.0

Baggage policy is punitive and no food service unless you pay for it makes it functional but no frills.

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Mediocre 3.6

Only the price

Flight was delay and they didn't supply any food

Tue, May 1
PDX
MDW
8h 18m
Fri, May 4
MDW
PDX
8h 24m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

SMF
ATL
Excellent 8.6

The crew were so polite and happy!

Those seats! UGH!

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

CZM
ATL
Excellent 10.0

easy but long day coming home

however on the initial trip to cozumel we where rerouted from kc to huntvilles therefore missing our connecting flight to cozumel so the airline was accomodating and reseated us on a flight to cancun instead and I was thankful but i know that that flight was cheaper when i booked this but i didnt want to make the treak to cancun and bus and then ferry to cozumel but ended up doing that anyway is there any way at all to be compensated for the diffrence I am not upset at all but that made for a really long day getting there Just putting it out there

Thu, Apr 12
PDX
ORD
3h 56m
Sat, Apr 14
ORD
PDX
4h 20m
Trip: 3 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Okay 4.0

Flight delayed until after 2am. Didn't like being nickeled and dimed for seat, overhead luggage.

Wed, May 2
PDX
ORD
3h 56m
Thu, May 3
ORD
PDX
4h 20m
Trip: 2 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Good 6.0

The price

Impossible to sleep

PDX
ORD
Good 6.0

Baggage policy is punitive and no food service unless you pay for it makes it functional but no frills.

Fri, May 11
EUG
ORD
7h 50m
Tue, May 15
ORD
EUG
15h 15m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 3
PDX
ORD
4h 04m
Sun, Apr 8
ORD
PDX
4h 29m
Trip: 6 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 18699 reviews
Overall
8.3
Boarding
8.4
Comfort
8.2
Crew
8.5
Entertainment
8.1
Food
7.7
LAX
SFO
Excellent 8.3

Loved the ambience!

Plane was a bit dirty from previous flight.

DEN
SFO
Good 7.3

Nice flight, friendly flight attendants.

It was delayed ☹️

JFK
SFO
Okay 4.0

The colors of the lights

Virgin has its own terminal in JFK (7), so they must have some amount of control over how things run. From the moment we got there, there was nothing but difficulty. Enormously long line (45 min wait). I booked my flight together with my boyfriend and we selected seats next to each other during booking. When we went to check in, they reassigned us to two middle seats. 6.5 hour flight. Then they make you pay for every detail, like WiFi, headsets, no small snacks, only 1 drink for the entire flight, etc. Any one of those things you’d probably have to pay for on other airlines, but together seemed over the top. We then landed and instead of heading to a gate, we sat on the runway for another 20 min. Again, no one of these things is out of the norm, but together made for a pretty miserable trip. Would have been significantly better if they just honored our original seating when we booked.

SFO
PSP
Okay 4.0

No seat Assignments given until right before boarding and we were not given seats together.

DAL
DCA
Excellent 10.0

This is my 2nd experience flying Virgin America. From the time I was dropped off at the airport till I arrived to Dallas, TX I had an amazing journey with Virgin America the atmosphere is phenomenal.

Non Applicable

Tue, Aug 14
EUG
ORD
6h 59m
Sat, Aug 18
ORD
EUG
8h 48m
Trip: 5 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 54591 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
MUC
IAD
Excellent 10.0

I am muslim, but I forgot to arrange the kind of food I would prefer during the flight, and the gentlement I talked to said let me see what I could do to help you about it, and few minutes later came up with muslim meal. I was really happy! Thank you all again.

Nothing.

DEN
IAH
Mediocre 2.0

Nothing

Never made it. Stuck in Denver.

DEN
LAX
Okay 5.0

Great crew and process

For the fare, the leg room is not enough for average 6'0 person to be comfortable for longer than an hour.

FSD
DEN
Mediocre 2.0

Friendly crew.

Stuck in Denver because our flight was delayed so we missed our connection to Houston. Couldn’t get a hotel voucher because they are claiming a weather delay (which there was none).

LGA
IAH
Good 6.3

I was told that I had to gate check my bags which had all of the necessities to travel with my child ( snacks, books, toys) due to it being a full flight. When I boarded, there were still several overhead storage bins completely empty. Very annoying. The crew could have physicallt assessed and checked before assuming due to flight capacity.

Fri, May 4
PDX
ORD
3h 56m
Sun, May 6
ORD
PDX
4h 20m
Trip: 3 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Good 6.0

The price

Impossible to sleep

PDX
ORD
Good 6.0

Baggage fee made it much much worse than I'd planned for

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

Sat, May 12
PDX
ORD
3h 56m
Sun, May 13
ORD
PDX
4h 20m
Trip: 2 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 3.6

Only the price

Flight was delay and they didn't supply any food

PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Good 6.0

Baggage fee made it much much worse than I'd planned for

PDX
ORD
Mediocre 2.0

It was a midnight flight. The people behind our seats talked all night loudly. The price for a carry on was astronomical. the seat charge is rediculus. The seats are uncomfortable and do not recline at all We will never fly Spirit air lines again

Tue, Mar 6
PDX
ORD
6h 39m
Wed, Mar 7
ORD
PDX
7h 57m
Trip: 2 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Okay 4.0

Flight delayed until after 2am. Didn't like being nickeled and dimed for seat, overhead luggage.

PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

PDX
ORD
Mediocre 3.6

Only the price

Flight was delay and they didn't supply any food

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

Wed, May 2
PDX
MDW
5h 52m
Fri, May 4
MDW
PDX
8h 24m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
DTW
Excellent 10.0

Pls see above

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

Tue, Apr 10
PDX
MDW
5h 48m
Fri, Apr 20
MDW
PDX
6h 22m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SMF
ATL
Excellent 8.6

The crew were so polite and happy!

Those seats! UGH!

ATL
DTW
Excellent 10.0

Pls see above

DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

Sat, Jun 9
PDX
ORD
3h 56m
Tue, Jun 12
ORD
PDX
4h 20m
Trip: 4 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 3.6

Only the price

Flight was delay and they didn't supply any food

PDX
ORD
Good 6.0

Baggage policy is punitive and no food service unless you pay for it makes it functional but no frills.

PDX
ORD
Good 6.0

Baggage fee made it much much worse than I'd planned for

PDX
ORD
Good 6.0

The price

Impossible to sleep

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

Wed, Apr 18
EUG
ORD
9h 45m
Sat, Apr 21
ORD
EUG
6h 50m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 2
PDX
MDW
7h 36m
Sat, Mar 10
MDW
PDX
7h 42m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

SMF
ATL
Excellent 8.6

The crew were so polite and happy!

Those seats! UGH!

Wed, Aug 8
PDX
ORD
3h 57m
Tue, Aug 21
ORD
PDX
4h 19m
Trip: 14 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Okay 4.0

Broken seat

PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Good 6.0

Baggage policy is punitive and no food service unless you pay for it makes it functional but no frills.

PDX
ORD
Good 7.0

The flight attendants were very nice.

That the flight was delayed twice and we left 3 hours after we were supposed to.

Wed, Mar 7
PDX
MDW
8h 21m
Sat, Mar 10
MDW
PDX
7h 42m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

ATL
DTW
Excellent 10.0

Pls see above

SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

Mon, Apr 9
EUG
ORD
9h 10m
Fri, Apr 13
ORD
EUG
7h 41m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Mar 10
MFR
ORD
8h 06m
Tue, Mar 13
ORD
MFR
7h 19m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jun 2
PDX
ORD
3h 56m
Tue, Jun 5
ORD
PDX
4h 20m
Trip: 4 days
4.7OkayShow reviews
Overall 4.7 Okay
Based on 146 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
PDX
ORD
Mediocre 2.0

Nothing

Hidden fees, water cost money, you save nothing with the cheap fair

PDX
ORD
Okay 4.0

Flight delayed until after 2am. Didn't like being nickeled and dimed for seat, overhead luggage.

PDX
ORD
Mediocre 2.0

Don't waste your time with this airline

PDX
ORD
Excellent 10.0

Very prompt, even early flights!

The spirit terminals are very chaotic. Attendants are very good, though.

PDX
ORD
Good 6.6

On time. Trabsparency. Whatever extra charge is clearlyentioned in the website.

Seats do not recline. At least drinking water should be free of charge

Oregon to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Oregon
Flight Price $138
Airlines Spirit Airlines, Delta, Virgin America, United
*
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