Roscoe Village Vacation Packages

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Top Holiday Package Deals in Roscoe Village

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $942, price is now CA $560 per person
CA $560
per person
Dec 5 - Dec 8
found 2 days ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (289 reviews)
The staff were excellent

Reviewed on Aug 21, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,595, price is now CA $1,507 per person
CA $1,507
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
You were being taken care of felt like home away from home good job to the staff at the Trump tower Chicago

Reviewed on Sep 12, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,630, price is now CA $1,016 per person
CA $1,016
per person
Nov 6 - Nov 10
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.

Reviewed on Sep 8, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,499, price is now CA $970 per person
CA $970
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Love the decor and style

Reviewed on Sep 12, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,007, price is now CA $655 per person
CA $655
per person
Dec 5 - Dec 8
found 2 days ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.

Reviewed on Sep 9, 2025

Where to stay in Roscoe Village

Find the best Roscoe Village areas and neighborhoods for the activities you enjoy most. Learn more about Roscoe Village
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

Roscoe Village Hotel Deals

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 $240 per night from Sep 22 to Sep 23
CA $240
CA $282 total
Sep 22 - Sep 23
includes taxes & fees
8.4/10 Very Good! (4,894 reviews)
"From the moment we walked in, early for our reservation, we were treated like the number one priority by every staff member. The bellman #johnnyBravo #JimmyNeutron #JohnnyDanger thank you for your comic relief after a long morning of travel and for keeping our belongings safe! The room was very clean ..."

Reviewed on Sep. 10, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 $194 per night from Sep 14 to Sep 15
CA $194
CA $228 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (9,133 reviews)
"Location, staff, and price were great!"

Reviewed on Sep. 12, 2025

Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Oct 2 to Oct 3
CA $251
CA $295 total
Oct 2 - Oct 3
includes taxes & fees
8.4/10 Very Good! (3,863 reviews)
"The staff was friendly and helpful."

Reviewed on Sep. 10, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,574 properties in Roscoe Village
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 Roscoe Village vacation package cost?
Our Roscoe Village packages, which start from as low as CA $560, are the easiest way to save money. Select your favorite hotels, flights and more to create your perfect getaway.
How do I get a cheap travel package to Roscoe Village?
You'll save a ton of money if you combine your hotels, car rentals and flights into a Roscoe Village vacation package. Sometimes cheap means fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 properties all over the world, so you'll always have plenty of options to choose from. Want to save even more? Add some exciting activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
Where should I stay in Roscoe Village?
Urban explorers come from all corners of the globe to experience Wrigley Field and Lincoln Park Zoo in Roscoe Village. Book a room near these must-see attractions and visit them at your leisure.
How far in advance should I book my Roscoe Village vacation?
The earlier, the better. Air carriers generally release flights up to a year ahead of departure, and this is a great opportunity to score some of the cheapest prices. Just been told you should take some vacation time in a few weeks? No sweat. Expedia are never short on fantastic bargains to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Roscoe Village travel package include?
Hotels, flights and rental cars — we've got them well covered. With Expedia, you can create your Roscoe Village package however you want. All you have to do is work out just what you need. Once you've made your booking, you can add on fun things like activities and experiences. The more you bundle, the more you save!
What should I know before booking a Roscoe Village travel package?
Get ready to save with an Expedia travel package. Bundle your flights, rental cars and hotels and score fabulous discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside villas, mountain cabins and even glamping tents!
Can I choose my airline with a Roscoe Village Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you definitely can. Simply choose the carrier you want and craft your ideal Roscoe Village vacation.
If I'm not able to travel, can I cancel my Roscoe Village vacation package?
Yes, it's possible to cancel your Roscoe Village booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Discover the most popular places to visit in Roscoe Village

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

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
Navy Pier

Navy Pier

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

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
94% of travellers recommend
Color Factory Chicago Ticket
Relax and enjoy the view

Chicago Architecture Center River Cruise aboard First Lady

CA $77
per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard First Lady
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.