Cheap flights from PDX to MDW (Portland Intl. to Midway Intl.)

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Cheap Flights from PDX to MDW starting at $64 One Way, $128 Round Trip

Prices starting at $128 for return flights and $64 for one-way flights to Midway Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 11 - Sat, May 18
PDX
Portland
MDW
Chicago
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 11 from Portland to Chicago, returning Sat, May 18, priced at $128 found 2 days ago
Sat, May 18 - Mon, May 20
PDX
Portland
MDW
Chicago
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 18 from Portland to Chicago, returning Mon, May 20, priced at $133 found 1 day ago
Tue, May 7 - Fri, May 10
PDX
Portland
MDW
Chicago
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 7 from Portland to Chicago, returning Fri, May 10, priced at $138 found 1 day ago
Sun, May 19 - Tue, May 21
PDX
Portland
MDW
Chicago
$143 Roundtrip, found 1 day ago
$143
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 19 from Portland to Chicago, returning Tue, May 21, priced at $143 found 1 day ago
Fri, May 17 - Tue, May 21
PDX
Portland
MDW
Chicago
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 17 from Portland to Chicago, returning Tue, May 21, priced at $148 found 1 day ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
The price is $106 per night from Apr 29 to Apr 30
$106
per night
Apr 29 - Apr 30
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast, and valet parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
7.8/10 Good! (2,531 reviews)
"Property is located in nice location, everything is accessible easily."

Reviewed on Apr 23, 2024

Best Western Grant Park Hotel
Hotel Chicago West Loop
Hotel Chicago West Loop
2.5 out of 5
1622 W Jackson Blvd, Chicago, IL
The price is $134 per night from Apr 28 to Apr 29
$134
per night
Apr 28 - Apr 29
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and onsite parking. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,000 reviews)
Great for quick trip-
"My significant other and I stayed over night for our first Blackhawks game (they won!). If you are on a tight budget like us, this place is perfect. We didnt spend a lot of time in the room but it was nice- appeared to have new paint and flooring. The bed was a little lumpy and pillows were a little ..."

Reviewed on Apr 15, 2024

Hotel Chicago West Loop
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $127 per night from Apr 28 to Apr 29
$127
per night
Apr 28 - Apr 29
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (6,587 reviews)
"A great older hotel. Very happy with my stay here."

Reviewed on Apr 23, 2024

Congress Plaza Hotel
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.

Hotels In Chicago

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $127 per night from Apr 28 to Apr 29
$127
per night
Apr 28 - Apr 29
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (6,587 reviews)
"A great older hotel. Very happy with my stay here."

Reviewed on Apr 23, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $149 per night from Apr 28 to Apr 29
$149
per night
Apr 28 - Apr 29
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,805 reviews)
"Did not care for offsite parking"

Reviewed on Apr 21, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $160 per night from Apr 28 to Apr 29
$160
per night
Apr 28 - Apr 29
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,855 reviews)
Great hotel!
"We really enjoyed our stay at the Eurostars Hotel. The customer service is superb and everyone was so kind and accommodating. Our room was great, however something must have been off with the ventilation/hvac system system because our room was humid and hot. Overall a great experience and located ..."

Reviewed on Apr 24, 2024

Eurostars Magnificent Mile
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.

Chicago Hotels With Airport Transportation

Motel 6 Elk Grove Village, IL - O'Hare
Motel 6 Elk Grove Village, IL - O'Hare
2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $65 per night from Apr 28 to Apr 29
$65
per night
Apr 28 - Apr 29
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,141 reviews)
"Room was very clean, quiet and service was friendly"

Reviewed on Apr 22, 2024

Motel 6 Elk Grove Village, IL - O'Hare
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
3 out of 5
777 East Grand Avenue, Bensenville, IL
The price is $85 per night from Apr 28 to Apr 29
$85
per night
Apr 28 - Apr 29
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.4/10 (1,001 reviews)
"Great place to stay at, close to the airport and has shuttles to and from the airport!"

Reviewed on Apr 19, 2024

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Comfort Suites Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport
3 out of 5
4200 North River Road, Schiller Park, IL
The price is $89 per night from May 8 to May 9
$89
per night
May 8 - May 9
Stay at this 3-star business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8.2/10 Very Good! (1,876 reviews)
"."

Reviewed on Apr 21, 2024

Comfort Suites Chicago O'Hare Airport
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.

Low Priced Chicago Hotels

Motel 6 Elk Grove Village, IL - O'Hare
Motel 6 Elk Grove Village, IL - O'Hare
2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $65 per night from Apr 28 to Apr 29
$65
per night
Apr 28 - Apr 29
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,141 reviews)
"Room was very clean, quiet and service was friendly"

Reviewed on Apr 22, 2024

Motel 6 Elk Grove Village, IL - O'Hare
Freehand Chicago
Freehand Chicago
4 out of 5
19 East Ohio Street, Chicago, IL
The price is $71 per night from Apr 29 to Apr 30
$71
per night
Apr 29 - Apr 30
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.6/10 Good! (1,002 reviews)
"Everyone has been great!"

Reviewed on Apr 20, 2024

Freehand Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
The price is $90 per night from Apr 29 to Apr 30
$90
per night
Apr 29 - Apr 30
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.2/10 (1,627 reviews)
"Perfect location to access local activities. Modest but clean accommodations."

Reviewed on Apr 22, 2024

Travelodge by Wyndham Downtown Chicago
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.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is $164 per night from Apr 28 to Apr 29
$164
per night
Apr 28 - Apr 29
Stay at this hotel in Chicago. Enjoy free breakfast, WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions ...
7.8/10 Good! (2,202 reviews)

Families like: Indoor pools, close to beach, bicycle rentals nearby, extra beds/cribs

Travelers say...
"Rooms were great. Comfortable and spacious."

Reviewed on Apr 23, 2024

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4 out of 5
511 North Columbus Drive, Chicago, IL
The price is $169 per night from May 12 to May 13
$169
per night
May 12 - May 13
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, WiFi, and room service. Our guests praise the breakfast and the helpful staff in ...
8.2/10 Very Good! (2,402 reviews)

Families like: Indoor pools, close to beach, bicycle rentals nearby, extra beds/cribs

Travelers say...
"Safe and walkable."

Reviewed on Apr 22, 2024

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
The price is $173 per night from May 26 to May 27
$173
per night
May 26 - May 27
Stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour health club. Our guests praise the breakfast and the helpful staff in our ...
8/10 Very Good! (1,179 reviews)

Families like: Indoor pools, close to beach, bicycle rentals, extra beds/cribs

Travelers say...
"The beauty of this historic hotel was wonderful! We enjoyed our stay there. It was a great meeting place for our family."

Reviewed on Apr 21, 2024

Palmer House a Hilton Hotel
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.

Map To Nearby Hotels

PDX to MDW Route Info

Origin Airport
Portland
Destination Airport
Chicago
Number Of Airlines Serving
1
Distance
1746 mi
Shortest Flight Departure Time
6:30AM CDT
Shortest Flight Departure Date
May 2
PDX Address & GPS
Address:
7000 NE Airport Way
Portland OR, 97218
United States
IATA Code:
PDX
Longitude:
-122.592901
Latitude:
45.588995
Time Zone:
America/Los_Angeles
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago

Frequently asked questions

Am I able to catch a flight from Portland, OR Airport (PDX-Portland Intl.) to Chicago, IL Airport (MDW-Midway Intl.) now?
The Covid-19 Travel Advisor can help you with queries about current travel restrictions and quarantine requirements when taking a plane flight from Portland, OR Airport (PDX-Portland Intl.) to Chicago, IL Airport (MDW-Midway Intl.).
Are there non-stop flights from PDX Airport to Chicago, IL Airport (MDW-Midway Intl.)?
Whether you’re heading off on an epic worldwide adventure or traveling for work purposes, a direct flight is the way to go. With Southwest Airlines you can get from Portland Intl. Airport (PDX) to MDW in one easy trip.
What is the shortest flight from PDX Airport to Chicago Airport?
Take the opportunity to chill out on the flight from Old Town Chinatown to West Lawn. The fastest flight time from Portland Airport to Chicago Airport is 5 hours and 34 minutes, which gives you more than enough time to enjoy a beverage or lose yourself in a good book.
How many hours flight from Portland Intl. Airport (PDX) to Chicago Airport?
Typically, the flight time from Portland, OR Airport (PDX-Portland Intl.) to Midway Airport takes 5 hours and 40 minutes. If your aim is to be as comfortable as you can, consider upgrading your seat using air miles or cash.
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago, IL Airport (MDW-Midway Intl.)?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago, IL Airport (MDW-Midway Intl.) have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago, IL Airport (MDW-Midway Intl.) with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago, IL Airport (MDW-Midway Intl.) without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What airlines have the most flights from PDX Airport to Chicago Airport?
Whether you pick an aisle or a window seat, you’ll jet to your destination easily and comfortably with Southwest Airlines. This quality airline offers 89 flights from PDX Airport to Midway Intl. Airport (MDW) per month.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.