Roseland Vacations from ￥337,288

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The Latest Roseland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥442,434, price is now ￥337,288 per person
￥337,288
per person
May 13 - May 18
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,719 reviews)
Great place to stay. Staff is very friendly

Reviewed on Mar 25, 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
Price was ￥619,115, price is now ￥437,907 per person
￥437,907
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Clean room, very nice front desk and great location

Reviewed on Mar 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥495,778, price is now ￥352,488 per person
￥352,488
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.

Reviewed on Mar 23, 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was ￥658,325, price is now ￥510,528 per person
￥510,528
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
We loved our stay. Two adults and our eight-year-old son took a weekend trip to Chicago. This hotel was very close to the field museum and walking distance to magnificent mile. Short Uber ride to nearby shopping and Willis Tower. The staff were awesome and upgraded our room at a low price. We felt very safe and staff were very helpful. The eighth floor had a beautiful pool, spa and sauna, great view of lake mi, open late too. We dined for breakfast at yoke and Niu B for dinner. Delicious. At checkout we purchased a future Hilton grand vacation at a great discount too. Let’s go. :)

Reviewed on Mar 25, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥568,890, price is now ￥460,718 per person
￥460,718
per person
May 14 - May 18
found 4 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit. We will be back in near future for surr!

Reviewed on Mar 24, 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
The price is ￥18,424 per night from Apr 1 to Apr 2
￥18,424
￥21,629 total
Apr 1 - Apr 2
includes taxes & fees
8/10 Very Good! (9,988 reviews)
I’ve stayed here before, and this time I was disappointed at the lack of cleanliness in the room and overall condition of it.

Reviewed on Mar 26, 2026

Congress Plaza Hotel
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 ￥19,474 per night from Apr 9 to Apr 10
￥19,474
￥22,860 total
Apr 9 - Apr 10
includes taxes & fees
9/10 Wonderful! (3,982 reviews)
Good location, parking only a couple blocks away, very clean and quiet room.

Reviewed on Mar 26, 2026

Hilton Chicago/Magnificent Mile Suites
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
The price is ￥23,316 per night from Apr 5 to Apr 6
￥23,316
￥27,371 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (5,775 reviews)
The pillows in the rooms were very hard and so was the bed. In the pool area there where not enough towels for people and it seemed very cold for a indoor pool.

Reviewed on Mar 25, 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.

Frequently asked questions

How much does a Roseland vacation package cost?
Get set to book, because a getaway to Roseland starts from just ￥337,288. When you combine your hotels, flights and car rentals into a vacation 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 vacation 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 vacation 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 fulfill those vacation 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 Center, Abbott Park and Bronzeville Childrens Museum are some top ones to add to your itinerary.
How far in advance should I book my Roseland vacation?
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 traveling 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 vacation is just clicks away.
Can I choose my airline with a Roseland Expedia vacation 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 vacation package?
Your situation can change suddenly, so yes, you can. You may be able to cancel or change your Roseland vacation 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.

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

￥3,985
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,236
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,860
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
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.