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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,207, price is now CA $798 per person
CA $798
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
everyone at the front desk was helpful and quite nice. room and amenities very clean. gym was well done for such a small space. would be great if there was a bathroom there. coffee and fresh fuit in the morning was awesome.
Reviewed on Jun 19, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,758, price is now CA $1,194 per person
CA $1,194
per person
Sep 10 - Sep 14
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.
Reviewed on Jun 20, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,439, price is now CA $1,687 per person
CA $1,687
per person
Sep 14 - Sep 17
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Usually this is one of the best property but this time they had water pipe burst and elevators werent working because of that. It was very inconvinient for this stay.
Reviewed on Jun 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,746, price is now CA $1,217 per person
CA $1,217
per person
Sep 14 - Sep 17
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
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
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.
Roscoe Village Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Jun 29 to Jun 30
CA $193
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,147 reviews)
"They were incredibly professional and accommodating. The staff was clear on expectations and were able to assist us on requests and information about the city. The rooms and hotel are gorgeous, the historical architecture was an amazing experience."
Reviewed on Jun 21, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Jul 5 to Jul 6
CA $197
CA $235 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (4,452 reviews)
"Clean room exelent"
Reviewed on Jun 19, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $183 per night from Jun 29 to Jun 30
CA $183
CA $217 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (1,601 reviews)
"Our stay was amazing! Staff was very helpful!"
Reviewed on Jun 19, 2026
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
Discover the most popular places to visit in Roscoe Village
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $69
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.