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Cheap flights from Oregon to Chicago from $70

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 9/10. 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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Cheap round-trip flights

Spirit Airlines Logo
12:07 pm - 9:32 pmPDX-ORD
7h 25m1 stop
Spirit Airlines Logo
12:46 pm - 7:23 pmORD-PDX
8h 37m1 stop
$150Spirit Airlines
Find Deal
Wed, Sep 17 - Sat, Sep 20
Frontier Logo
12:43 pm - 11:53 pmPDX-ORD
9h 10m1 stop
Frontier Logo
6:50 am - 11:48 amORD-PDX
6h 58m1 stop
$152Frontier
Find Deal
Wed, Oct 15 - Fri, Oct 17
Logo
6:05 am - 11:59 pmPDX-ORD
15h 54m1 stop
Logo
12:46 pm - 7:23 pmORD-PDX
8h 37m1 stop
$163
Find Deal
Thu, Sep 18 - Sat, Sep 20
Logo
2:16 pm - 9:32 pmBOI-ORD
6h 16m1 stop
Logo
6:20 am - 3:00 pmORD-BOI
9h 40m1 stop
$167
Find Deal
Sat, Sep 20 - Sat, Sep 27
Alaska Airlines Logo
4:34 pm - 12:03 amBOI-ORD
6h 29m1 stop
Alaska Airlines Logo
8:00 am - 2:36 pmORD-BOI
7h 36m1 stop
$190Alaska Airlines
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Tue, Sep 23 - Sat, Oct 4
Delta Logo
5:25 am - 1:03 pmBOI-MDW
6h 38m1 stop
Delta Logo
9:20 am - 2:15 pmMDW-BOI
5h 55m1 stop
$191Delta
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Tue, Sep 30 - Sat, Oct 4
Hawaiian Airlines Logo
4:34 pm - 12:03 amBOI-ORD
6h 29m1 stop
Hawaiian Airlines Logo
8:00 am - 3:54 pmORD-BOI
8h 54m1 stop
$192Hawaiian Airlines
Find Deal
Wed, Sep 10 - Wed, Sep 24
Hawaiian Airlines Logo
2:28 pm - 12:03 amBOI-ORD
8h 35m1 stop
Hawaiian Airlines Logo
8:00 am - 2:36 pmORD-BOI
7h 36m1 stop
$193Hawaiian Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
Delta Logo
5:25 am - 1:03 pmBOI-MDW
6h 38m1 stop
Delta Logo
7:15 pm - 11:59 pmMDW-BOI
5h 44m1 stop
$194Delta
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Tue, Sep 23 - Sat, Oct 4
Alaska Airlines Logo
2:28 pm - 12:03 amBOI-ORD
8h 35m1 stop
Alaska Airlines Logo
10:00 am - 3:54 pmORD-BOI
6h 54m1 stop
$203Alaska Airlines
Find Deal
Wed, Sep 24 - Fri, Oct 3

Hawaiian Airlines flights from Oregon to Chicago

Our best Hawaiian Airlines deals on Oregon to Chicago flight tickets
Hawaiian Airlines
Sep 10
BOI4:34 pmBoise Air Term. Gowen Fld
6h 29m
1 stop
ORD12:03 amChicago O'Hare Intl
Sep 24
ORD8:00 amChicago O'Hare Intl
8h 54m
1 stop
BOI3:54 pmBoise Air Term. Gowen Fld
$192
Find similar
Hawaiian Airlines
Sep 30
BOI2:28 pmBoise Air Term. Gowen Fld
8h 35m
1 stop
ORD12:03 amChicago O'Hare Intl
Oct 4
ORD8:00 amChicago O'Hare Intl
7h 36m
1 stop
BOI2:36 pmBoise Air Term. Gowen Fld
$193
Find similar
Hawaiian Airlines
Sep 20
BOI4:34 pmBoise Air Term. Gowen Fld
6h 29m
1 stop
ORD12:03 amChicago O'Hare Intl
Sep 27
ORD5:45 pmChicago O'Hare Intl
7h 23m
1 stop
BOI12:08 amBoise Air Term. Gowen Fld
$208
Find similar

Spirit Airlines flights from Oregon to Chicago

Our best Spirit Airlines deals on Oregon to Chicago flight tickets
Spirit Airlines
Sep 17
PDX12:07 pmPortland
7h 25m
1 stop
ORD9:32 pmChicago O'Hare Intl
Sep 20
ORD12:46 pmChicago O'Hare Intl
8h 37m
1 stop
PDX7:23 pmPortland
$150
Find similar
Spirit Airlines
Sep 3
PDX7:52 pmPortland
6h 58m
1 stop
ORD4:50 amChicago O'Hare Intl
Sep 6
ORD12:46 pmChicago O'Hare Intl
8h 37m
1 stop
PDX7:23 pmPortland
$160
Find similar
Spirit Airlines
Sep 6
PDX8:18 pmPortland
13h 33m
1 stop
ORD11:51 amChicago O'Hare Intl
Sep 10
ORD9:00 amChicago O'Hare Intl
12h 23m
1 stop
PDX7:23 pmPortland
$162
Find similar

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 August 14, 2025.
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

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/17

12:07 pm-9:32 pm

1 stop7h 25m

Chicago O'Hare Intl

Sat 9/20

12:46 pm-7:23 pm

1 stop8h 37m

$150

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 10/15

12:43 pm-11:53 pm

1 stop9h 10m

Chicago O'Hare Intl

Fri 10/17

6:50 am-11:48 am

1 stop6h 58m

$152

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 9/18

6:05 am-11:59 pm

1 stop15h 54m

Chicago O'Hare Intl

Sat 9/20

12:46 pm-7:23 pm

1 stop8h 37m

$163

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sat 9/20

2:16 pm-9:32 pm

1 stop6h 16m

Chicago O'Hare Intl

Sat 9/27

6:20 am-3:00 pm

1 stop9h 40m

$167

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 9/23

4:34 pm-12:03 am

1 stop6h 29m

Chicago O'Hare Intl

Sat 10/4

8:00 am-2:36 pm

1 stop7h 36m

$190

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 9/30

5:25 am-1:03 pm

1 stop6h 38m

Chicago Midway

Sat 10/4

9:20 am-2:15 pm

1 stop5h 55m

$191

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 9/10

4:34 pm-12:03 am

1 stop6h 29m

Chicago O'Hare Intl

Wed 9/24

8:00 am-3:54 pm

1 stop8h 54m

$192

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 9/30

2:28 pm-12:03 am

1 stop8h 35m

Chicago O'Hare Intl

Sat 10/4

8:00 am-2:36 pm

1 stop7h 36m

$193

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 9/23

5:25 am-1:03 pm

1 stop6h 38m

Chicago Midway

Sat 10/4

7:15 pm-11:59 pm

1 stop5h 44m

$194

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 9/24

2:28 pm-12:03 am

1 stop8h 35m

Chicago O'Hare Intl

Fri 10/3

10:00 am-3:54 pm

1 stop6h 54m

$203

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 $272. 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 $283.

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 Friday when prices can be found for as low as $452. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Oregon to Chicago for around $570.

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 $309. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $508.

What is the cheapest Oregon to Chicago flight route?

Fly from Portland to Chicago Midway 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 $359 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 $298 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 23% 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

$70

Fastest flight time

3h 20m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Oregon in the past 72 hours is $70. The best round-trip flight deal from Oregon to Chicago found on momondo in the last 72 hours is $150.
The fastest flight from Oregon to Chicago takes 3h 20m
Direct flights go from Oregon to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • 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 $86Free CancellationRating
6.3
8,045 reviews
Search Spirit Airlines flights
FrontierPriceFrom $108Free CancellationRating
5.8
3,219 reviews
Search Frontier flights
DeltaPriceFrom $123Free CancellationRating
8.0
7,980 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $178Free CancellationRating
7.8
2,656 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $191Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $218Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,916 reviews
Search United Airlines flights
SouthwestPriceFrom $238Free CancellationRating
8.0
4,244 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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