Roseland Vacations from $394
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Roseland Vacation
Our Roseland vacation packages are a simple and practical way to plan and book your next break. Discover the heart and soul of this unique neighborhood without the bother of planning everything yourself. Begin your trip to Roseland with a visit to nearby attractions such as Abbott Park, Harborside International Golf Center and A. Philip Randolph Pullman Porter Museum. Expedia will help put your travel plans into action. Book your ultimate Roseland vacation now.
The Latest Roseland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,044, price is now $763 per person
$763
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Gorgeous hotel in a prime location off of the Magnificent Mile. Staff were incredible, buffet breakfast was the perfect way to start our day.
My only issue was the amount of air freshener scent throughout the property. It was ok in the lobby but so so strong on our floor leading to our room. It was nauseating. Would definitely stay again and recommend
Reviewed on Nov 7, 2026
Where to stay in Roseland
Find the best Roseland areas and neighborhoods for the activities you enjoy most. Learn more about Roseland
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Roseland Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,120 reviews)
"The hot water pressure was quite weak on"
Reviewed on Nov 7, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $149 total per night from Nov 9 to Nov 10
$149 total
Nov 9 - Nov 10
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundable
$115 nightly
The price is $137 total per night from Dec 6 to Dec 7
$137 total
Dec 6 - Dec 7
Total with taxes and fees
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.
Stay near popular Roseland attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.