Roseland Vacation Packages

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    Save up to CA $4,200 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,676, price is now CA $1,151 per person
CA $1,151
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,854 reviews)
We contacted the property about checking luggage early, no problem. Check in was quick as well as checking out. Markets and pharmacy about a block away. Restaurants, bars, pubs landmarks all within walking distance. Red line and brown line L train about 8 minute walk. Our room was a little small but was comfortable and had everything we needed, very clean and for being downtown surprisingly quiet. Would recommend and would return.

Reviewed on Jul 24, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,590, price is now CA $1,522 per person
CA $1,522
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Good hotel, I’m just not entirely sure if the amenities and overall experience justify the price. Other than big building, prime location and a nice looking hobby, the hotel doesn’t really offer any differential amenity to any random half-priced hotel a few blocks away.

Reviewed on Jul 25, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,173, price is now CA $1,496 per person
CA $1,496
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (504 reviews)

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 CA $2,391, price is now CA $1,676 per person
CA $1,676
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $2,666, price is now CA $1,880 per person
CA $1,880
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,271 reviews)

Where to stay in Roseland

Find the best Roseland areas and neighborhoods for the activities you enjoy most. Learn more about Roseland
A busy city street with tall buildings, a bus, and cars.

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

Roseland Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Aug 24 to Aug 25
CA $255
CA $303 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very good! (1,839 reviews)
"The bar staff and manager were the absolute BEST!!! Thank you so much for trying so hard to find the random items I wanted for cocktails!!! Everything we had was very well done and made with utmost care! Absolutely A+++!!!"

Reviewed on Jul 25, 2026

The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $281 per night from Aug 9 to Aug 10
CA $281
CA $334 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,937 reviews)
"The booking info is incorrect"

Reviewed on Jul 25, 2026

The Wade
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
The price is CA $264 per night from Aug 9 to Aug 10
CA $264
CA $360 total
Aug 9 - Aug 10
includes taxes & fees
Omni Chicago Hotel
See all 4,280 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 $1,151. 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.

Stay near popular Roseland attractions

Abbott Park

Abbott Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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.