Roseland Holidays

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    Save up to €900 when you book a flight and hotel together*

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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
Save 100% on your flight
Price was €790, price is now €509 per person
€509
per person
24 Jul - 28 Jul
found 18 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
Place is in a great location but once you go past the lobby its very dated. Small rooms and had lots of trouble getting in touch with the front desk when we needed something.

Reviewed on 7 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,041, price is now €598 per person
€598
per person
24 Jul - 28 Jul
found 18 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on 6 May 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,130, price is now €676 per person
€676
per person
24 Jul - 28 Jul
found 18 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (462 reviews)
The rooms were very clean!

Reviewed on 4 May 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,101, price is now €706 per person
€706
per person
24 Jul - 28 Jul
found 18 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again

Reviewed on 6 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,726, price is now €1,131 per person
€1,131
per person
24 Jul - 28 Jul
found 18 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
I love everything in the hotel everything

Reviewed on 4 May 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

Downtown Chicago

4 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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is €114 per night from 25 May to 26 May
€114
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,689 reviews)
Place is in a great location but once you go past the lobby its very dated. Small rooms and had lots of trouble getting in touch with the front desk when we needed something.

Reviewed on 7 May 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is €145 per night from 25 May to 26 May
€145
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,178 reviews)
Our go to hotel when visiting Chicago! It’s centrally located and has everything we need at a hotel! Will definitely come back!

Reviewed on 7 May 2026

River 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
The price is €185 per night from 27 May to 28 May
€185
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (4,082 reviews)
Beautiful hotel, very impressed with the cleanliness, space in the room and the breakfast. So pleased we chose this hotel as the location was excellent 👌

Reviewed on 7 May 2026

Hotel Riu Plaza Chicago
See all 4,405 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 €509. 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

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
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

5/5(1 review)

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
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€38
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€39
per adult
100% of travellers recommend
Chicago Sightseeing River and 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.