Downtown Skokie Vacations from ￥274,160

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The Latest Downtown Skokie Vacation Packages

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

Hotel Riu Plaza Chicago

Downtown Chicago
￥274,160
per person
Nov 6 - Nov 9
found 9 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
The property waa clean and spacious Staff were very nice and helpful. The location was perfect a short walk or drive to alot of places ans the best of all was that A Garrett's popcorn shop waa right across the street!

Reviewed on Aug 11, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥308,437
per person
Nov 6 - Nov 9
found 9 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Sentral Michigan Avenue

Sentral Michigan Avenue

Downtown Chicago
￥494,270
per person
Sep 14 - Sep 21
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,237 reviews)
Great value. Right on Michigan Ave. front desk staff very helpful.

Reviewed on Aug 11, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥360,552
per person
Sep 18 - Sep 22
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Freehand Chicago

Freehand Chicago

Downtown Chicago
￥279,254
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.8/10 Good! (3,233 reviews)
The overall property is dark and the carpets and walls on the hotel floors are dirty. My room also had dirty walls and a dirty shade that did not work well. While the sheets were seemingly clean, as was the bathroom, I was hesitant to walk in bare feet on the carpet. One of the two elevators was always broken down pretty much my entire stay. I prepaid for the week so I had to tough it out, but I will not be back.

Reviewed on Aug 10, 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.

Find hotels in Downtown Chicago
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.

Find hotels in Magnificent Mile
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.

Find hotels in River North
A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Find hotels in Theatre District

Downtown Skokie Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,474
￥19,588 total
Sep 8 - Sep 9
includes taxes & fees
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
￥22,555
￥26,816 total
Aug 31 - Sep 1
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
￥35,605
￥41,797 total
Sep 5 - Sep 6
includes taxes & fees
8.4/10 Very Good! (2,388 reviews)
"Extremely well located and expensive, of course. The staff were well-trained. Very over-air conditioned. Decor straight out of the 70s?"

Reviewed on Aug 11, 2026

Hilton Chicago O'Hare Airport
See all 4,496 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.

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

￥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

￥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge 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.