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Cheap flights from Oregon to Chicago from $87

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oregon to Chicago departing on 4/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Oregon to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:28 pm - 9:18 pm
EUG
-
ORD
6h 50m
1 stop
Delta Logo
6:00 pm - 11:58 pm
ORD
-
EUG
7h 58m
1 stop
$177Delta
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
6:35 am - 4:35 pm
EUG
-
MDW
8h 00m
2 stops
Southwest Logo
6:30 am - 10:45 am
MDW
-
EUG
6h 15m
1 stop
$180Southwest
Tue, Apr 21 - Tue, Apr 28
Delta Logo
6:30 am - 9:18 pm
EUG
-
ORD
12h 48m
2 stops
Delta Logo
6:00 pm - 11:58 pm
ORD
-
EUG
7h 58m
1 stop
$182Delta
Tue, Apr 14 - Tue, Apr 21
Frontier Logo
1:22 pm - 11:01 pm
BOI
-
ORD
32h 39m
2 stops
Frontier Logo
9:42 pm - 12:27 pm
ORD
-
BOI
15h 45m
1 stop
$211Frontier
Tue, May 5 - Wed, May 13
Frontier Logo
9:54 am - 5:50 am
PDX
-
ORD
17h 56m
1 stop
Frontier Logo
7:21 pm - 11:50 am
ORD
-
PDX
18h 29m
1 stop
$223Frontier
Fri, Apr 17 - Wed, Apr 22
United Airlines Logo
10:56 pm - 5:00 am
PDX
-
ORD
4h 04mnonstop
United Airlines Logo
9:30 pm - 11:59 pm
ORD
-
PDX
4h 29mnonstop
$235United Airlines
Thu, Apr 23 - Thu, Apr 30
American Airlines Logo
1:45 pm - 8:11 pm
PDX
-
ORD
4h 26mnonstop
American Airlines Logo
7:29 am - 9:59 am
ORD
-
PDX
4h 30mnonstop
$236American Airlines
Thu, Jun 4 - Wed, Jun 10
Alaska Airlines Logo
8:14 pm - 6:40 am
RDM
-
ORD
8h 26m
1 stop
Alaska Airlines Logo
5:52 pm - 11:58 pm
ORD
-
RDM
8h 06m
1 stop
$300Alaska Airlines
Tue, Apr 21 - Tue, Apr 28
United Airlines Logo
1:55 pm - 12:59 am
RDM
-
ORD
9h 04m
1 stop
United Airlines Logo
6:25 am - 11:55 am
ORD
-
RDM
7h 30m
1 stop
$312United Airlines
Tue, Apr 21 - Tue, Apr 28
Alaska Airlines Logo
8:14 pm - 6:40 am
RDM
-
ORD
8h 26m
1 stop
Alaska Airlines Logo
5:52 pm - 11:58 pm
ORD
-
RDM
8h 06m
1 stop
$317Alaska Airlines
Tue, Apr 21 - Tue, Apr 28

Alaska Airlines flights from Oregon to Chicago

Our best Alaska Airlines deals on Oregon to Chicago flight tickets
Alaska Airlines
May 1
EUG5:42 pmEugene
17h 31m
1 stop
ORD1:13 pmChicago O'Hare Intl
May 5
ORD3:52 pmChicago O'Hare Intl
9h 02m
1 stop
EUG10:54 pmEugene
$257
Alaska Airlines
Apr 25
BOI4:38 pmBoise Air Term. Gowen Fld
13h 02m
1 stop
ORD6:40 amChicago O'Hare Intl
May 2
ORD6:00 amChicago O'Hare Intl
8h 52m
1 stop
BOI1:52 pmBoise Air Term. Gowen Fld
$295
Alaska Airlines
Apr 29
EUG1:23 pmEugene
8h 36m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 2
ORD3:52 pmChicago O'Hare Intl
9h 02m
1 stop
EUG10:54 pmEugene
$297

American Airlines flights from Oregon to Chicago

Our best American Airlines deals on Oregon to Chicago flight tickets
American Airlines
Jun 4
PDX1:45 pmPortland
4h 26m
ORD8:11 pmChicago O'Hare Intl
Jun 10
ORD7:29 amChicago O'Hare Intl
4h 30m
PDX9:59 amPortland
$236
American Airlines
Apr 18
PDX6:22 amPortland
4h 10m
ORD12:32 pmChicago O'Hare Intl
Apr 21
ORD8:19 pmChicago O'Hare Intl
4h 37m
PDX10:56 pmPortland
$251
American Airlines
Apr 13
PDX3:16 pmPortland
4h 18m
ORD9:34 pmChicago O'Hare Intl
Apr 18
ORD11:52 amChicago O'Hare Intl
4h 32m
PDX2:24 pmPortland
$258

momondo Fare Finder

 
Customize your flight search to find flights from Oregon to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 26, 2026.
Use the filters below to find and compare flights from Oregon to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 4/14

12:28 pm-9:18 pm

1 stop6h 50m

Chicago O'Hare Intl

Tue 4/21

6:00 pm-11:58 pm

1 stop7h 58m

$177

EugeneChicago

EUG - MDW

EUGMDW

Eugene

Tue 4/21

6:35 am-4:35 pm

2 stops8h 00m

Chicago Midway

Tue 4/28

6:30 am-10:45 am

1 stop6h 15m

$180

EugeneChicago

EUG - ORD

EUGORD

Eugene

Tue 4/14

6:30 am-9:18 pm

2 stops12h 48m

Chicago O'Hare Intl

Tue 4/21

6:00 pm-11:58 pm

1 stop7h 58m

$182

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 5/5

1:22 pm-11:01 pm

2 stops32h 39m

Chicago O'Hare Intl

Wed 5/13

9:42 pm-12:27 pm

1 stop15h 45m

$211

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 4/17

9:54 am-5:50 am

1 stop17h 56m

Chicago O'Hare Intl

Wed 4/22

7:21 pm-11:50 am

1 stop18h 29m

$223
Quickest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 4/23

10:56 pm-5:00 am

Nonstop4h 04m

Chicago O'Hare Intl

Thu 4/30

9:30 pm-11:59 pm

Nonstop4h 29m

$235

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 6/4

1:45 pm-8:11 pm

Nonstop4h 26m

Chicago O'Hare Intl

Wed 6/10

7:29 am-9:59 am

Nonstop4h 30m

$236

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 4/21

8:14 pm-6:40 am

1 stop8h 26m

Chicago O'Hare Intl

Tue 4/28

5:52 pm-11:58 pm

1 stop8h 06m

$300

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 4/21

1:55 pm-12:59 am

1 stop9h 04m

Chicago O'Hare Intl

Tue 4/28

6:25 am-11:55 am

1 stop7h 30m

$312

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 4/21

8:14 pm-6:40 am

1 stop8h 26m

Chicago O'Hare Intl

Tue 4/28

5:52 pm-11:58 pm

1 stop8h 06m

$317

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Oregon to Chicago

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 month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Oregon, with most prices found around $237. If you’re not able to fly to Chicago in January, then August is your next best option. Flight prices from Oregon to Chicago during August average around $288.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $422. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Oregon to Chicago for around $527.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Oregon to Chicago during this time can be as low as $305. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $467.

What is the cheapest Oregon to Chicago flight route?

Fly from Portland to Chicago O'Hare Intl for the best Oregon - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Oregon when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $338 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Oregon for as low as $270 on momondo.

What cabin class options are available on Oregon to Chicago flights?

There are 4 cabin classes available to choose from on Oregon to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Oregon to Chicago flights?

You could potentially save up to 1% on your flight if you consider stops on a Oregon to Chicago flight.

Cheap Oregon to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oregon to Chicago

Best Price Found

$168

Fastest flight time

3h 20m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Oregon in the past 72 hours is $168. The best round-trip flight deal from Oregon to Chicago found on momondo in the last 72 hours is $328.
The fastest flight from Oregon to Chicago takes 3h 20m
Direct flights go from Oregon to Chicago every day.
There are 3 airports in Chicago. From Oregon there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • When did momondo last update prices for flights from Oregon to Chicago?

    Prices for flights from Oregon to Chicago were last updated today.

  • How many operators does momondo search for flights from Oregon to Chicago?

  • How old do you have to be to fly from Oregon to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oregon to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Oregon to Chicago?

Best airlines flying from Oregon to Chicago

Compare and see reviews for airlines that fly from Oregon to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $93Free CancellationRating
6.3
8,543 reviews
Search Spirit Airlines flights
FrontierPriceFrom $96Free CancellationRating
5.7
3,016 reviews
Search Frontier flights
DeltaPriceFrom $99Free CancellationRating
7.9
8,331 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $125Free CancellationRating
7.8
2,840 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $179Free CancellationRating
7.1
11,493 reviews
Search American Airlines flights
United AirlinesPriceFrom $206Free CancellationRating
7.4
9,483 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $208Free CancellationRating
7.9
12,112 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $231Free CancellationRating
8.0
4,333 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Oregon to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Oregon to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Oregon to Chicago with flexible booking policies on momondo?

Flights from Oregon to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Oregon to Chicago?

Once all potential Oregon to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Oregon to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Oregon and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport