Downtown Skokie Vacation Packages

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Top Holiday Package Deals in Downtown Skokie

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,261
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
The bed was really good. It was so comfortable that I slept like a baby. And the Breakfast was good also. All stuffs are nice , they always greet me with smil. I’ll recommend RIU Plaza Hotel to my friends if they go to Chicago.

Reviewed on Aug 29, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,361
per person
Nov 15 - Nov 21
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (556 reviews)
Great! But parking was bad.

Reviewed on Aug 26, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,474
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
My sister and I came to Chicago from Baltimore to see the Obama Presidential Center. When I researched hotels to stay at in Chicago I was very impressed with Swissotel ratings. I could’ve made a better choice. We didn’t get to see everything we wanted to see, but when we do come back to Chicago Swissotel is definitely where we’ll be staying. So if you’re planning on coming to Chicago Swissotel is the best choice.

Reviewed on Aug 29, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $3,160
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,615
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on Aug 27, 2026

Where to stay in Downtown Skokie

Find the best Downtown Skokie areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Skokie
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.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Downtown Skokie Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $148
CA $176 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,200 reviews)
"Cool old building with lots of history; however, the room was freezing cold with no ability to adjust the temperature, the water never stayed hot, the bed was firm like a board, and the tub clogged so we were showering with 3 inches of standing water. Regardless, the staff was kind and it did the ..."

Reviewed on Aug 29, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $194
CA $231 total
Sep 21 - Sep 22
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $324
CA $381 total
Sep 18 - Sep 19
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 4,494 properties in Downtown Skokie
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
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Beach Vacations
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Family Vacations
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Golf Vacations
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Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Stay near popular Downtown Skokie attractions

Skokie Theatre

8.2/10 (59 reviews)
You can make plans for a show at Skokie Theatre during your trip to Skokie. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.
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Illinois Science and Technology Park

7.6/10 (29 reviews)
Illinois Science and Technology Park is just one of the places to see in Skokie, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
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 $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
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.