Roseland Holidays

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Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was €379, price is now €295 per person
€295
per person
31 Oct - 2 Nov
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
We were dead tired from a long flight from Turkey the day before. We slept well most of the night but still did not want to drag our heavy bags to Terminal 5 via the light rail. The hotel graciously transported us directly to the outdoor check in and we were on our way to security an hour ahead of our schedule! Thanks. The only improvement would be to service the slightly noisy air conditioner in our room.

Reviewed on 20 Sept 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €954, price is now €672 per person
€672
per person
31 Oct - 2 Nov
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.

Reviewed on 8 Sept 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was €564, price is now €431 per person
€431
per person
31 Oct - 2 Nov
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,008 reviews)
Best hotel ever! The staff was incredible. The location was premium-you could be at the “bean” in a couple minutes!! The bed was so cozy. The place was clean and beautiful. There was a snack daily. It really was so fantastic!

Reviewed on 17 Sept 2025

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was €584, price is now €469 per person
€469
per person
31 Oct - 2 Nov
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
8.6/10 Excellent! (1,907 reviews)
Bartenders were really good at jobs

Reviewed on 16 Sept 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Price was €545, price is now €441 per person
€441
per person
31 Oct - 2 Nov
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
8.4/10 Very Good! (3,910 reviews)
Property was close to event i needed to attend. Allowed for an early check in so I could prepare for event. Staff helpful.

Reviewed on 22 Sept 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 which includes 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

Top hotels in Roseland

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €134 per night from 23 Sept to 24 Sept
€134
23 Sept - 24 Sept
includes taxes & fees
7.8/10 Good! (9,265 reviews)
"Big hotel with lots of floors."

Reviewed on 22 Sept 2025

Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €176 per night from 2 Oct to 3 Oct
€176
2 Oct - 3 Oct
includes taxes & fees
8.4/10 Very Good! (3,921 reviews)
"Everything was great. Downtown location was awesome. Close to everything. We walked to a restaurant. Would definitely stay here again."

Reviewed on 19 Sept 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
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
The price is €161 per night from 20 Oct to 21 Oct
€161
20 Oct - 21 Oct
includes taxes & fees
8.8/10 Excellent! (2,901 reviews)
"Great location, close to different restaurants and coffee shops. Sadly the pool was closed when I was there but it looked like the property was very well maintained. Staff was so nice upon check in. Our room was nice and comfortable! Enjoyed my stay and will be back!!"

Reviewed on 19 Sept 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,279 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 €295. 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

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

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

Michigan Avenue

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
Navy Pier

Navy Pier

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

€42
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€38
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

€38
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.