Roseland Vacations from $508

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $821, price is now $508 per person
$508
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Staff was friendly and helpful. Room was clean and the bed was comfortable.

Reviewed on Mar 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,236, price is now $654 per person
$654
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Amazing service, staff were very attentive and friendly! Buffet selection was top tier.

Reviewed on Mar 23, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $1,103, price is now $663 per person
$663
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
The stay as wonderful

Reviewed on Mar 22, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $933, price is now $601 per person
$601
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Everything was perfect. We own a cleaning company so when traveling or staycationing we check the beds for bedbugs, lice and any other critters. Everything was pristine. I also let the phone staff know we were staying for my wife’s birthday and requested a higher room and they did say they couldn’t guarantee that but not only did they give us a higher floor they gave us a corner room also! Probably on of the best views in the building. Thank you for that. The area is also less congested than other parts of downtown. There’s SOME street parking nearby. Walkable distance to 7Eleven, Whole Foods and Jewel. Love this boutique hotel better than the large chain ones. Customer service was also great. We will be back.

Reviewed on Mar 23, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,488, price is now $1,654 per person
$1,654
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Clean rooms and friendly staff

Reviewed on Mar 22, 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 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
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $151 total per night from Apr 1 to Apr 2
$151 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (10,001 reviews)
Rooms were in far condition but poorly maintained.

Reviewed on Mar 23, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $183 total per night from Apr 6 to Apr 7
$183 total
Apr 6 - Apr 7
Total with taxes and fees
9.4/10 Exceptional! (3,612 reviews)
Amazing service, staff were very attentive and friendly! Buffet selection was top tier.

Reviewed on Mar 23, 2026

Hotel Riu Plaza 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
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Apr 5 to Apr 6
$153 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (5,779 reviews)
Breakfast fresh. Pool was finr

Reviewed on Mar 23, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,399 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

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

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
Chicago Skyline at North Beach

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$26
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
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.