Skokie Vacation Packages

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Your Skokie Vacation

There's no better way to escape than with one of our vacation packages to Skokie. The diversity and progressive thinking are a couple of the compelling reasons you'll want to stay in this awesome city. Like to get out and explore? Northwestern University, Loyola University Chicago and Aragon Ballroom are three of the leading places to visit during your trip to Skokie. Your ideal Skokie vacation is a couple of clicks away. Search hotels, airfares and more on Expedia for a getaway that's tailored to suit your style.

Top Skokie Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was CA $878, price is now CA $589 per person
CA $589
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
7.4/10 Good! (1,004 reviews)
Quick stay in between traveling. The bed and bedding comfortable. Room is spacious. Staff friendly.

Reviewed on Aug. 30, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,246, price is now CA $789 per person
CA $789
per person
Oct 22 - Oct 25
found 24 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,350, price is now CA $876 per person
CA $876
per person
Oct 22 - Oct 25
found 24 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,831, price is now CA $1,198 per person
CA $1,198
per person
Oct 25 - Oct 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.

Reviewed on Aug. 24, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $1,922, price is now CA $1,279 per person
CA $1,279
per person
Oct 22 - Oct 25
found 24 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

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Skokie Hotel Deals

Holiday Inn Chicago North Shore by IHG

Holiday Inn Chicago North Shore by IHG

3 out of 5
5300 West Touhy Ave, Skokie, IL
Fully refundable
The price is CA $191 per night from Sep 3 to Sep 4
CA $191
CA $219 total
Sep 3 - Sep 4
includes taxes & fees
Holiday Inn Chicago North Shore by IHG
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 2 to Sep 3
CA $194
CA $228 total
Sep 2 - Sep 3
includes taxes & fees
Congress Plaza Hotel
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
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Sep 4 to Sep 5
CA $231
CA $271 total
Sep 4 - Sep 5
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
See all 4,948 properties in 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Skokie

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

What to do in Skokie

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Skokie
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.