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.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,383, price is now CA $889 per person
CA $889
per person
Jun 5 - Jun 10
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (480 reviews)
The staff was friendly and the bed was very comfortable! Easy to find parking, many food options within walking distance.

Reviewed on Apr 21, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,873, price is now CA $1,261 per person
CA $1,261
per person
Jun 19 - Jun 22
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
I was blown away by our room. So big, clean. Also the 8th floor amenities were amazing! Will definitely be back! Everything about this place was incredible and so clean!

Reviewed on Apr 26, 2026

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Price was CA $1,524, price is now CA $1,030 per person
CA $1,030
per person
Jun 11 - Jun 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (327 reviews)
Rooms were modern, clean and comfortable. The staff was amazing! The concierge host, Charles, was the best. So kind, helpful, genuine and friendly.

Reviewed on Apr 27, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,812, price is now CA $1,256 per person
CA $1,256
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
We had a great time! Room was clean, spacious, and nice views! Staff was friendly and helpful. Will stay again

Reviewed on Apr 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,254, price is now CA $1,578 per person
CA $1,578
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,853 reviews)
Fabulous food and outstanding bar and staff with a phenomenal panoramic view of the heart of Chicago. Love!!!

Reviewed on Apr 27, 2026

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Skokie Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Apr 28 to Apr 29
CA $119
CA $181 total
Apr 28 - Apr 29
includes taxes & fees
8.2/10 Very Good! (2,647 reviews)
great location. clean. convenient

Reviewed on Apr 27, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from May 25 to May 26
CA $161
CA $192 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,139 reviews)
Great place,staff and location we will be back again for the 3rd time

Reviewed on Apr 27, 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundable
The price is CA $150 per night from May 25 to May 26
CA $150
CA $178 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,465 reviews)
I was only in town for one day. But it was an easy seamless check-in. The room was clean and bathroom was clean. Everything in the room work and I had no need to call or any assistance. The checkout was very simple was done on my phone as I walk down the hallway before leaving.

Reviewed on Apr 26, 2026

Club Quarters Hotel, Central Loop, Chicago
See all 4,917 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

Wrigley Field

4.5/5(159 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 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 $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
94% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.