Roseland Vacation Packages

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Roseland

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.

Reviewed on Jan 6, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,044, price is now CA $743 per person
CA $743
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,155, price is now CA $828 per person
CA $828
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.

Reviewed on Feb 7, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $949, price is now CA $708 per person
CA $708
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
Great stay. Would come again.

Reviewed on Jan 19, 2026

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
Price was CA $952, price is now CA $723 per person
CA $723
per person
Apr 21 - Apr 25
found 16 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
My room was very clean, which I appreciated. We booked a suite, but the first one opened directly into the bedroom, and being on the first floor, I didn’t feel comfortable with that layout. I requested a room change, and the staff handled it quickly and professionally, which I really appreciated. One thing that was a bit confusing was the inconsistency between suites—some had a full kitchen while others only had a range top. It would be helpful to know that in advance when booking. Overall, the stay was quiet and peaceful during the week, which was exactly what we wanted. When we arrived on Saturday afternoon, the atmosphere was completely different—lots of people, plenty of activity, and a lively environment. The only real downside was that the room felt drafty. We ended up putting a towel under the door to help block the cold air. Aside from those small issues, it was a comfortable stay with a good stay.

Reviewed on Jan 16, 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 CA $122 per night from Feb 8 to Feb 9
CA $122
CA $143 total
Feb 8 - Feb 9
includes taxes & fees
8/10 Very Good! (9,839 reviews)
Great a+++

Reviewed on Feb 1, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Feb 21 to Feb 22
CA $190
CA $263 total
Feb 21 - Feb 22
includes taxes & fees
8.4/10 Very Good! (2,597 reviews)
Some of the nicest people you'll ever meet! Excellent location for a Bears game stay, walking distance to Soldier Field.

Reviewed on Feb 1, 2026

Hilton Chicago
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Feb 15 to Feb 16
CA $126
CA $147 total
Feb 15 - Feb 16
includes taxes & fees
8.6/10 Excellent! (2,285 reviews)
Awesome quite hotel beds are amazing great location

Reviewed on Feb 5, 2026

DoubleTree by Hilton Chicago - Magnificent Mile
See all 4,638 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Roseland vacation package cost?
Get set to book, because a getaway to Roseland starts from just CA $707. 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 central business district, a city and a sporting event

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
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

4.5/5(19 reviews)

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
Navy Pier featuring a sunset and rides

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

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
96% of travellers recommend
Color Factory Chicago 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.