Roseland Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to €185 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
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
per person
15 May - 20 May
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8/10 Very Good! (1,524 reviews)
Love booking a room there

Reviewed on 23 Mar 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
15 May - 20 May
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,310 reviews)
Great stay on St. Patrick's Day weekend.

Reviewed on 24 Mar 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
15 May - 20 May
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,046 reviews)
The Emily Hotel is a phenomenal place. Leo at the front desk was amazing at checking us in and making our experience so much better. Great stay!! And we look forward to going back for rooftop movie nights!!!

Reviewed on 23 Mar 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
15 May - 20 May
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Excellent, just what anyone would expect from this brand.

Reviewed on 25 Mar 2025

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
per person
15 May - 20 May
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,608 reviews)
The staff was great, it was nice they have a free cocktail bar at night where you get two adult beverages everyday. The breakfast was decent for a free breakfast. the bad, the hotel was under construction which was not communicated at time of booking. Only one elevator was operational so the wait times were long every time. The walls in the hotel were paper thin. The room next to us was empty but we could hear the kids two rooms down our entire stay. Pictures online show a walk in shower, not what our room had, and the beds were not comfortable.

Reviewed on 24 Mar 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 featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Roseland

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
The price is €138 per night from 21 Apr to 22 Apr
€138
includes taxes & fees
21 Apr - 22 Apr
8.2/10 Very Good! (3,756 reviews)
"This is a great property for families. It had a large breakfast area. A lot of places to hang out outside of the room. The view from the room was great too."

Reviewed on 24 Mar 2025

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €107 per night from 13 Apr to 14 Apr
€107
includes taxes & fees
13 Apr - 14 Apr
8.6/10 Excellent! (3,958 reviews)
"Great stay!"

Reviewed on 24 Mar 2025

River Hotel
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is €118 per night from 3 Apr to 4 Apr
€118
includes taxes & fees
3 Apr - 4 Apr
8.6/10 Excellent! (1,025 reviews)
"They made us feel right at home and accommodated us"

Reviewed on 24 Mar 2025

Crowne Plaza Chicago West Loop by IHG
See all 3,963 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.

Frequently asked questions

How much does a Roseland holiday package cost?
Get set to book, because a getaway to Roseland starts from just €1,274. When you combine your hotels, flights and car rentals into a holiday package, you’ll score the best deals.
How do I get a cheap travel package to Roseland?
Simply by bundling. Hotels, rental cars and flights — combine whatever you need into a Roseland holiday package and save. Score even more bargains when you include extras such as tours or experiences to your booking. But that’s not the only impressive part. You have the freedom to put together your holiday your way. We offer more than 550 partner airlines and 1,000,000 hotel options throughout the world, so that everyone has an opportunity to travel and fulfil those holiday dreams.
Where should I stay in Roseland?
With lots to explore in Roseland, it makes sense to lock in a hotel close to its attractions. Harborside International Golf Centre, Abbott Park and Bronzeville Childrens Museum are some top ones to add to your itinerary.
How far in advance should I book my Roseland holiday?
While not all air carriers advertise tickets early, you can usually look up international flights on Expedia up to a year in advance. This is the time when you can bag some fantastic deals. If you’re purchasing tickets last minute, you might still get lucky. Low prices occasionally emerge only weeks prior to departure.
What does an Expedia Roseland travel package include?
That depends on what you’re after. If you’re travelling alone, you might decide to combine hotels and flights. Bringing the whole crew to Roseland? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the freedom to tailor your travel package.
What should I know before booking a Roseland travel package?
Discover deals that fit your budget with an Expedia package. Airfares, hotels, rental cars — we’ve got them all. You’ll save big dollars just for bundling your bookings. Whether you’re going on a ski adventure or sunning yourself on a warm beach, your dream holiday is just clicks away.
Can I choose my airline with a Roseland Expedia holiday package?
Yes — that’s one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 airline partners throughout the world, so you have options galore when arranging your Roseland escape.
If I'm not able to travel, can I cancel my Roseland holiday package?
Your situation can change suddenly, so yes, you can. You may be able to cancel or change your Roseland holiday package at no cost if you’ve booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may impose a fee. Want more information? Have a look at our Customer Service Portal. We’ll help make sure your trip goes off without a hitch.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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

Flyover in Chicago

Flyover in Chicago

€35
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

€45
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

€41
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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.