Roseland Vacation Packages

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Top Holiday Package Deals in Roseland

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 19 - Jul. 22
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 9 - Sep. 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Love this property. Whenever we visit Chicago this is where we stay. It’s lovely.

Reviewed on Jun. 12, 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 9 - Sep. 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,114 reviews)
The hotel was great and guest services were awesome. Noted my late arrival due to delayed flight. The hotel is right on Michigan and the bus stops right in front. The rooms are comfortable and well designed. However, I wouldn't recommend eating at ALK. What a rip. for $6, I got about 10 spears of grilled asparagus! I know food prices and labor have gone up but this is ridiculous.

Reviewed on Jun. 8, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 9 - Sep. 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (210 reviews)
Great room - fabulous fitness center. Easy access to grocery stores to stock fridge. Room is furnished with all amenities.

Reviewed on Jun. 9, 2024

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 9 - Sep. 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,167 reviews)
Location… kids loved it

Reviewed on Jun. 13, 2024

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

4 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 Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips 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 CA $212 per night from Jun. 16 to Jun. 17
CA $212
CA $249 total
includes taxes & fees
Jun 16 - Jun 17
7.6/10 Good! (6,949 reviews)
"The properties age is quite obvious, but it looks reasonably well maintained and my room was clean and had all necessary amenities"

Reviewed on Jun. 14, 2024

Congress Plaza Hotel
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 CA $262 per night from Jul. 1 to Jul. 2
CA $262
CA $308 total
includes taxes & fees
Jul 1 - Jul 2
8/10 Very Good! (2,370 reviews)
"I love the location of this hotel. It’s vey convenient to walk everywhere. Breakfast is awesome. Front desk is lukewarm not the friendliest but not the worse. One is not even paying attention and charged me again even though I prepaid my stayed in Expedia. It’s still showing pending in my CC so I’m ..."

Reviewed on Jun. 12, 2024

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is CA $223 per night from Jul. 3 to Jul. 4
CA $223
CA $262 total
includes taxes & fees
Jul 3 - Jul 4
8.6/10 Excellent! (2,947 reviews)
"Perfect place with a water view. Walkable"

Reviewed on Jun. 13, 2024

River Hotel
See all 3,938 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.

Explore other types of vacation packages

All Inclusive Vacations

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Frequently asked questions

How much does a Roseland vacation package cost?
Get set to book, because a getaway to Roseland starts from just CA $1,085. 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

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $255
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

CA $64
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
See all activities in Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.