Best Flight From Portland Intl. To ORD

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Amazing PDX to ORD Flight Deals

The cheapest flights to O'Hare Intl. were $256 for round trip flights and $111 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Nov 10 - Fri, Nov 13
PDX
Portland
ORD
Chicago
$256 Roundtrip, found 5 days ago
$256
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Nov 10 from Portland to Chicago, returning Fri, Nov 13, priced at $256 found 5 days ago
Wed, Nov 11 - Fri, Nov 13
PDX
Portland
ORD
Chicago
$272 Roundtrip, found 6 days ago
$272
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Wed, Nov 11 from Portland to Chicago, returning Fri, Nov 13, priced at $272 found 6 days ago
Wed, Jan 6 - Sun, Jan 10
PDX
Portland
ORD
Chicago
$278 Roundtrip, found 5 days ago
$278
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Wed, Jan 6 from Portland to Chicago, returning Sun, Jan 10, priced at $278 found 5 days ago
Mon, Nov 23 - Thu, Nov 26
PDX
Portland
ORD
Chicago
$280 Roundtrip, found 4 days ago
$280
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Mon, Nov 23 from Portland to Chicago, returning Thu, Nov 26, priced at $280 found 4 days ago
Mon, Nov 23 - Thu, Nov 26
PDX
Portland
ORD
Chicago
$281 Roundtrip, found 4 days ago
$281
Roundtrip
found 4 days ago
Select United flight, departing Mon, Nov 23 from Portland to Chicago, returning Thu, Nov 26, priced at $281 found 4 days ago
Tue, Nov 10 - Fri, Nov 13
PDX
Portland
ORD
Chicago
$285 Roundtrip, found 5 days ago
$285
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, Nov 10 from Portland to Chicago, returning Fri, Nov 13, priced at $285 found 5 days ago

Hotels near O'Hare Intl. Airport (ORD)

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$212 nightly
The price is $248 total per night from Nov 22 to Nov 23
$248 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Opens in a new windowHilton Chicago O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd Rosemont IL
$127 nightly
The price is $145 total per night from Nov 24 to Nov 25
$145 total
Nov 24 - Nov 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
8.6/10 Excellent! (2,895 reviews)
"Better than average. Nothing outstanding."

Reviewed on Oct 27, 2026

Opens in a new windowCrowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$144 nightly
The price is $164 total per night from Nov 22 to Nov 23
$164 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
9/10 Wonderful! (3,290 reviews)
"Friendly staff and my room was well maintained !"

Reviewed on Oct 27, 2026

Opens in a new windowHyatt Regency O'Hare Chicago
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Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
$132 nightly
The price is $150 total per night from Nov 24 to Nov 25
$150 total
Nov 24 - Nov 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
9/10 Wonderful! (3,211 reviews)
"Impossible to get a receipt for my stay, which is very frustrating."

Reviewed on Oct 26, 2026

Opens in a new windowHoliday Inn Chicago O'Hare – Rosemont by IHG
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
10249 Irving Park Road Schiller Park IL
$144 nightly
The price is $165 total per night from Oct 29 to Oct 30
$165 total
Oct 29 - Oct 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Opens in a new windowFour Points by Sheraton Chicago O'Hare Airport
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
3001 South Mannheim Road Des Plaines IL
$119 nightly
The price is $140 total per night from Nov 24 to Nov 25
$140 total
Nov 24 - Nov 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Des Plaines. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
8.8/10 Excellent! (2,071 reviews)
"If going to Allstate for any reason best affordable stay"

Reviewed on Oct 26, 2026

Opens in a new windowHoliday Inn Express & Suites Chicago O'Hare Airport by IHG
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

4 out of 5
5460 North River Road Rosemont IL
$127 nightly
The price is $144 total per night from Nov 24 to Nov 25
$144 total
Nov 24 - Nov 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
8.8/10 Excellent! (1,007 reviews)
"Adequate for overnight layover. Free shuttle to and from airport. Decent restaurant at hotel, large clean room."

Reviewed on Oct 27, 2026

Opens in a new windowDoubleTree by Hilton Chicago O'Hare Airport - Rosemont
Sheraton Suites Chicago O'Hare

Sheraton Suites Chicago O'Hare

3.5 out of 5
6501 N Mannheim Rd Rosemont IL
$152 nightly
The price is $173 total per night from Nov 22 to Nov 23
$173 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
Opens in a new windowSheraton Suites Chicago O'Hare
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.