Roseland Vacations from $229

Book a Hotel + Flight or Car together to unlock savings

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.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $344, price is now $229 per person
$229
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,006 reviews)
I love the way they check on you to make sure everything is okay.

Reviewed on Sep 23, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,067, price is now $635 per person
$635
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay

Reviewed on Sep 19, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $532, price is now $324 per person
$324
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Beautiful new hotel, gorgeous rooftop with delicious food. Hotel staff are super friendly and helpful.

Reviewed on Sep 30, 2025

The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
Price was $426, price is now $275 per person
$275
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (146 reviews)
Popular with drunks that party way past reasonable quiet hours.

Reviewed on Sep 27, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $947, price is now $636 per person
$636
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!

Reviewed on Sep 28, 2025

Where to stay in Roseland

Find the best Roseland areas and neighborhoods for the activities you enjoy most. Learn more about Roseland
Downtown Chicago showing a city

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Roseland Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$175 nightly
The price is $206 total per night from Oct 2 to Oct 3
$206 total
Oct 2 - Oct 3
Total with taxes and fees
7.8/10 Good! (9,376 reviews)
"Very Clean Hotel, me and my friend enjoyed our stay here. It is an older hotel but the room was really nice"

Reviewed on Sep 30, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $152 total per night from Oct 29 to Oct 30
$152 total
Oct 29 - Oct 30
Total with taxes and fees
7.8/10 Good! (2,411 reviews)
"I really liked the vibe and location, easy walk to many Classic Chicago scenes. My room was very clean but small and dark. The sink faucet and shower head both leaked. Both should be monitored and repaired in order to maintain an environmental consciousness."

Reviewed on Sep 29, 2025

Freehand 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
$195 nightly
The price is $229 total per night from Oct 19 to Oct 20
$229 total
Oct 19 - Oct 20
Total with taxes and fees
8.4/10 Very Good! (5,017 reviews)
"staff friendly"

Reviewed on Sep 30, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,303 properties in Roseland
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Roseland

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.