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 - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Price was CA $1,046, price is now CA $789 per person
CA $789
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (MDW)
8.4/10 Very Good! (1,004 reviews)
Yes everything was good

Reviewed on Feb 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,634, price is now CA $1,131 per person
CA $1,131
per person
May 22 - May 25
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel

Reviewed on Mar 10, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was CA $1,133, price is now CA $800 per person
CA $800
per person
Apr 26 - May 1
found 9 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.4/10 Very Good! (1,705 reviews)
Room decent. Bartendars very friendly.

Reviewed on Mar 10, 2026

Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Downtown Chicago
Price was CA $1,954, price is now CA $1,461 per person
CA $1,461
per person
May 29 - Jun 1
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,197 reviews)
We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early.

Reviewed on Mar 9, 2026

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Skokie Hotel Deals

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 $131 per night from Apr 1 to Apr 2
CA $131
CA $154 total
Apr 1 - Apr 2
includes taxes & fees
8/10 Very Good! (9,942 reviews)
I like this hotel. It’s simple, clean, no frills and gets the job done. Hallways carpets are a little worse for wear but the room serves the purpose - you get what you reserve! - and you’re close to everything. It’s a “go to” for me.

Reviewed on Mar 10, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is CA $187 per night from Mar 24 to Mar 25
CA $187
CA $258 total
Mar 24 - Mar 25
includes taxes & fees
9.4/10 Exceptional! (3,507 reviews)
Clean, amazing terrace, bad and breakfast.

Reviewed on Mar 10, 2026

Hotel Riu Plaza Chicago
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
The price is CA $166 per night from Mar 22 to Mar 23
CA $166
CA $195 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (5,724 reviews)
The room was perfect, the bar open up at 4pm and they have happy hour at 5:30-7 they do have a little spot to get snack they are over price but they have water if you need any in the front desk .

Reviewed on Mar 10, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,994 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.
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Discover the most popular places to visit in Skokie

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(19 reviews)

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 featuring a sunset and rides

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Skokie

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $36
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Skokie

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