Downtown Skokie Vacations from ₩1,032,580

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Downtown Skokie Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
₩1,032,580
per person
Nov 2 - Nov 6
found 12 hours ago
Roundtrip non-stop flight included
Lubbock (LBB) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
₩1,198,921
per person
Nov 2 - Nov 6
found 12 hours ago
Roundtrip non-stop flight included
Lubbock (LBB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on Aug 17, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
₩1,047,899
per person
Nov 2 - Nov 6
found 12 hours ago
Roundtrip non-stop flight included
Lubbock (LBB) to Chicago (ORD)
8.2/10 Very Good! (2,899 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
₩1,395,188
per person
Nov 2 - Nov 6
found 12 hours ago
Roundtrip non-stop flight included
Lubbock (LBB) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Fairmont maybe an old hotel but it is well maintained hotel. With large rooms, great views of the skyline especially at night from our window. And Le Labo toiletries is a plus. Also Many great restaurants nearby

Reviewed on Aug 17, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
₩1,333,003
per person
Nov 2 - Nov 6
found 12 hours ago
Roundtrip non-stop flight included
Lubbock (LBB) to Chicago (ORD)
9.4/10 Exceptional! (3,808 reviews)

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.

Find hotels in The Loop
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 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.

Find hotels in Lincoln Park

Downtown Skokie Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
₩162,449
₩193,135 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
₩202,400
₩240,634 total
Aug 30 - Aug 31
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
₩344,817
₩404,780 total
Sep 12 - Sep 13
includes taxes & fees
8.4/10 Very Good! (2,412 reviews)
"Was not a good hotel."

Reviewed on Aug 17, 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.
See properties

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.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.