Roseland Vacations from $295

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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.
Holiday Inn Chicago O'Hare Area by IHG

Holiday Inn Chicago O'Hare Area by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.8/10 Good! (1,001 reviews)
This hotel was clean, amazing breakfast, service and staff were friendly as can be and helpful! Stayed for three days and loved it!

Reviewed on Jun 1, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
great location. only issue experienced was the in-room TV. it was challenging to use due to built in technologlgy. example, channel guide was a URL code scan on your phone, but you could not see anything on the TV

Reviewed on Jun 29, 2025

Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (47 reviews)
The area has a lot of fun nightlife and things to do, but it was surprisingly quiet in our room! The room itself was clean and felt quite private, despite being in the shared suite. All the other guests we met were kind and courteous too! We drove, and parking was somewhat difficult but the map provided showing parking rules for surrounding roads made that much easier! The only thing we didn’t love was the provided breakfast, my partner told me they would have loved for some sausage or eggs to be included.

Reviewed on Jun 15, 2025

Comfort Inn Chicago Schaumburg - O'Hare Airport

Comfort Inn Chicago Schaumburg - O'Hare Airport

2.5 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 8
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7/10 Good! (840 reviews)
The mall to go shopping was near..

Reviewed on Jun 28, 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (211 reviews)
other than the mold on the soap dispenser this hotel is beautiful

Reviewed on Jun 27, 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

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $169 total per night from Jul 6 to Jul 7
$169 total
Jul 6 - Jul 7
Total includes taxes and fees
8.8/10 Excellent! (2,354 reviews)
"Hard to located without sign took us 30 minutes to find hotel"

Reviewed on Jun 29, 2025

Hilton Chicago/Magnificent Mile Suites
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
$193 nightly
The price is $220 total per night from Jul 2 to Jul 3
$220 total
Jul 2 - Jul 3
Total includes taxes and fees
9/10 Wonderful! (1,932 reviews)
"Elevators were really slow like uncomfortably slow and not efficient at all so"

Reviewed on Jun 29, 2025

InterContinental Chicago Magnificent Mile by IHG
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $157 total per night from Jul 1 to Jul 2
$157 total
Jul 1 - Jul 2
Total includes taxes and fees
7.8/10 Good! (8,892 reviews)
"It was in a great location. My friends and I had a great stay here and were super close to Millenium park. Bus stops were close and the hotel was great overall. Parking was expensive so make sure to book it somewhere else beforehand as well. You will find better deals that way."

Reviewed on Jun 29, 2025

Congress Plaza Hotel
See all 4,201 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
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
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

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
92% 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.