Portage Park Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Portage Park Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
$801
per person
Dec 9 - Dec 13
found 10 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Really nice place
Reviewed on Oct 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$910
per person
Dec 9 - Dec 13
found 10 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
It's our second time staying at the RIU and it's always an amazing experience. The staff is amazing, the cleanliness, the food, the overall experience of staying at the RIU is amazing. Thank you all for the wonderful experience!
Reviewed on Oct 4, 2026
Level Chicago Fulton Market
Downtown Chicago
$928
per person
Dec 9 - Dec 13
found 10 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Everything at my residence was phenomenal. The bed was very comfortable, the kitchen was fully stocked with proper utensils. Make sure you look under the sink for the paper towel. The only setback was there should have been a make up/vanity mirror for the guest.
One more thing with the windows open, you hear traffic really loudly, but when closed you hear nothing it is a very good property!!! I propose on this trip!! thank you so much for the opportunity.
Reviewed on Oct 4, 2026
The Talbott, Autograph Collection
Downtown Chicago
$935
per person
Dec 9 - Dec 13
found 9 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
$931
per person
Dec 9 - Dec 13
found 10 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Very clean!
Reviewed on Oct 4, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
$1,085
per person
Dec 9 - Dec 13
found 10 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
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Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
River Hotel
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Hilton Chicago
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Eurostars Magnificent Mile
660 North State Street Chicago IL
Book a stay at this 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 ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
The Wade
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
Freehand Chicago
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
The Godfrey Hotel Chicago
127 West Huron, at LaSalle Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Sports Illustrated Resorts Chicago
203 N Wabash Ave Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Oct 22 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 4 days ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 2 hours ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197
Roundtrip
found 3 hours ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 2 hours ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 2 hours ago
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