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Cheap flights from Portland to Illinois from $61

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Illinois departing on 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:47 pm - 12:12 amPDX-ORD
9h 25m1 stop
Multiple Airlines Logo
7:44 pm - 3:00 pmORD-PDX
21h 16m2 stops
$239Multiple Airlines
Find Deal
Thu, Dec 25 - Tue, Dec 30
Frontier Logo
12:47 pm - 12:12 amPDX-ORD
9h 25m1 stop
Frontier Logo
10:01 pm - 10:34 amORD-PDX
14h 33m1 stop
$240Frontier
Find Deal
Sun, Dec 21 - Sun, Jan 11
Alaska Airlines Logo
5:30 pm - 5:04 amPDX-ORD
9h 34m1 stop
Alaska Airlines Logo
7:45 am - 12:36 pmORD-PDX
6h 51m1 stop
$242Alaska Airlines
Find Deal
Sat, Mar 7 - Sat, Mar 14
United Airlines Logo
11:59 pm - 5:52 amPDX-ORD
3h 53mnonstop
United Airlines Logo
9:05 am - 11:48 amORD-PDX
4h 43mnonstop
$243United Airlines
Find Deal
Mon, Nov 24 - Thu, Nov 27
Alaska Airlines Logo
5:49 pm - 2:39 pmPDX-ORD
18h 50m1 stop
Alaska Airlines Logo
2:12 pm - 4:50 pmORD-PDX
4h 38mnonstop
$245Alaska Airlines
Find Deal
Fri, Dec 5 - Thu, Dec 18
Southwest Logo
6:15 am - 12:10 pmPDX-MDW
3h 55mnonstop
Southwest Logo
9:50 pm - 12:20 amMDW-PDX
4h 30mnonstop
$247Southwest
Find Deal
Fri, Dec 5 - Sun, Dec 7
United Airlines Logo
12:55 pm - 9:58 pmPDX-STL
7h 03m1 stop
United Airlines Logo
1:35 pm - 6:06 pmSTL-PDX
6h 31m1 stop
$249United Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
11:37 am - 5:52 pmPDX-ORD
4h 15mnonstop
American Airlines Logo
9:57 am - 12:38 pmORD-PDX
4h 41mnonstop
$252American Airlines
Find Deal
Wed, Dec 10 - Mon, Dec 15
Southwest Logo
7:15 am - 5:05 pmPDX-MDW
7h 50m1 stop
Southwest Logo
5:15 pm - 10:30 pmMDW-PDX
7h 15m1 stop
$256Southwest
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Fri, Dec 5 - Tue, Dec 9
American Airlines Logo
11:37 am - 5:52 pmPDX-ORD
4h 15mnonstop
American Airlines Logo
9:57 am - 12:38 pmORD-PDX
4h 41mnonstop
$269American Airlines
Find Deal
Wed, Dec 3 - Sun, Dec 14

Frontier flights from Portland to Illinois

Our best Frontier deals on Portland to Illinois flight tickets
Frontier
Dec 21
PDX12:47 pmPortland
9h 25m
1 stop
ORD12:12 amChicago O'Hare Intl
Jan 11
ORD10:01 pmChicago O'Hare Intl
14h 33m
1 stop
PDX10:34 amPortland
$240
Find similar
Frontier
Nov 10
PDX3:26 pmPortland
6h 49m
1 stop
ORD12:15 amChicago O'Hare Intl
Nov 13
ORD6:00 amChicago O'Hare Intl
7h 56m
1 stop
PDX11:56 amPortland
$252
Find similar
Frontier
Nov 17
PDX3:26 pmPortland
6h 49m
1 stop
ORD12:15 amChicago O'Hare Intl
Nov 23
ORD9:38 pmChicago O'Hare Intl
12h 26m
1 stop
PDX8:04 amPortland
$253
Find similar

American Airlines flights from Portland to Illinois

Our best American Airlines deals on Portland to Illinois flight tickets
American Airlines
Dec 10
PDX11:37 amPortland
4h 15m
ORD5:52 pmChicago O'Hare Intl
Dec 15
ORD9:57 amChicago O'Hare Intl
4h 41m
PDX12:38 pmPortland
$252
Find similar
American Airlines
Dec 3
PDX11:37 amPortland
4h 15m
ORD5:52 pmChicago O'Hare Intl
Dec 14
ORD9:57 amChicago O'Hare Intl
4h 41m
PDX12:38 pmPortland
$269
Find similar
American Airlines
Dec 6
PDX1:28 pmPortland
4h 18m
ORD7:46 pmChicago O'Hare Intl
Dec 10
ORD8:10 amChicago O'Hare Intl
4h 37m
PDX10:47 amPortland
$287
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Portland to Illinois 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 November 6, 2025.
Use the filters below to find and compare flights from Portland to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 12/25

12:47 pm-12:12 am

1 stop9h 25m

Chicago O'Hare Intl

Tue 12/30

7:44 pm-3:00 pm

2 stops21h 16m

$239

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 12/21

12:47 pm-12:12 am

1 stop9h 25m

Chicago O'Hare Intl

Sun 1/11

10:01 pm-10:34 am

1 stop14h 33m

$240

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 3/7

5:30 pm-5:04 am

1 stop9h 34m

Chicago O'Hare Intl

Sat 3/14

7:45 am-12:36 pm

1 stop6h 51m

$242

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 11/24

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

Thu 11/27

9:05 am-11:48 am

Nonstop4h 43m

$243

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 12/5

5:49 pm-2:39 pm

1 stop18h 50m

Chicago O'Hare Intl

Thu 12/18

2:12 pm-4:50 pm

Nonstop4h 38m

$245

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

6:15 am-12:10 pm

Nonstop3h 55m

Chicago Midway

Sun 12/7

9:50 pm-12:20 am

Nonstop4h 30m

$247

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Wed 12/3

12:55 pm-9:58 pm

1 stop7h 03m

Lambert-St Louis

Wed 12/10

1:35 pm-6:06 pm

1 stop6h 31m

$249

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/10

11:37 am-5:52 pm

Nonstop4h 15m

Chicago O'Hare Intl

Mon 12/15

9:57 am-12:38 pm

Nonstop4h 41m

$252

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

7:15 am-5:05 pm

1 stop7h 50m

Chicago Midway

Tue 12/9

5:15 pm-10:30 pm

1 stop7h 15m

$256

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/3

11:37 am-5:52 pm

Nonstop4h 15m

Chicago O'Hare Intl

Sun 12/14

9:57 am-12:38 pm

Nonstop4h 41m

$269

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 Illinois from

How to get the cheapest flight ticket from Portland to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Portland is in August. Flight prices, which tend to average around $293, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of August, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $293.

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

The cheapest day to depart from Portland to Illinois is on a Friday when prices can be found for as low as $434. Flights from Portland to Illinois on a Sunday will generally be more expensive and average around $557. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the afternoon. Flights from Portland to Illinois during this time can be as low as $316. Flights in the morning are often more expensive with an average ticket price of $493.

What is the cheapest Portland to Illinois flight route?

Fly from Portland to Chicago Midway for the best Portland - Illinois flight prices

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

You are more likely to see cheaper flights to Illinois from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $358 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Portland for as low as $293 on momondo.

What cabin class options are available on Portland to Illinois flights?

There are 4 cabin classes available to choose from on Portland to Illinois 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 Portland to Illinois flights?

No. A direct flight is the cheapest option for a flight between Portland to Illinois.

Cheap Portland to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Illinois

Best Price Found

$186

Fastest flight time

3h 50m

Direct flights

Every day

Airports in Illinois

2 airports
The best one-way flight to Illinois from Portland in the past 72 hours is $186. The best round-trip flight deal from Portland to Illinois found on momondo in the last 72 hours is $287.
The fastest flight from Portland to Illinois takes 3h 50m
Direct flights go from Portland to Illinois every day.
There are 2 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • When did momondo last update prices for flights from Portland Airport to Illinois?

    Prices for flights from Portland Airport to Illinois are refreshed on a daily basis.

  • How many operators does momondo search for flights from Portland Airport to Illinois?

  • How old do you have to be to fly from Portland Airport to Illinois?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Portland Airport to Illinois.

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

    The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Portland to Illinois?

Best airlines flying from Portland to Illinois

Compare and see reviews for airlines that fly from Portland to Illinois with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $94Free CancellationRating
5.8
3,116 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $119Free CancellationRating
6.3
8,114 reviews
Search Spirit Airlines flights
DeltaPriceFrom $123Free CancellationRating
7.9
8,004 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $125Free CancellationRating
7.8
2,804 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $192Free CancellationRating
7.2
11,041 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $197Free CancellationRating
8.0
11,243 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $222Free CancellationRating
7.4
9,003 reviews
Search United Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,240 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Illinois?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Portland to Illinois. momondo saves you time and could save you money on your trip.

Can I find flights from Portland to Illinois with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Portland to Illinois flights to just show those with flexible booking policies.

How can momondo help me find flights from Portland to Illinois?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Illinois from Portland.

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

Yes. momondo can track prices for Portland to Illinois flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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