Book Exclusive Skokie Vacation Packages

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Skokie flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Mar. 14 - Mar. 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
Mar. 9 - Mar. 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Mar. 14 - Mar. 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Feb. 18 - Feb. 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
per person
Feb. 2 - Feb. 5
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Top Skokie hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $150 per night
CA $150
CA $176 total
includes taxes & fees
26 Dec - 27 Dec
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Free WiFi
Restaurant
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $149 per night
CA $149
CA $175 total
includes taxes & fees
8 Jan - 9 Jan 2025
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $200 per night
CA $200
CA $277 total
includes taxes & fees
10 Jan - 11 Jan 2025
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Free cancellation
The price is CA $159 per night
CA $159
CA $187 total
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pool
Free WiFi
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $138 per night
CA $138
CA $162 total
includes taxes & fees
12 Jan - 13 Jan 2025
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Spa
Free WiFi
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $201 per night
CA $201
CA $278 total
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Pool
Pet-friendly
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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.

Popular places to visit

Magnificent Mile - River North which includes signage, a city and night scenes

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

Wrigley Field

4.5/5(158 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(141 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

McCormick Place

Skokie Vacations

You don't have to be full of local knowledge to have an incredible time in Skokie, but you should know a few basic things before you head off.

Around 12 miles (19 kilometers) northwest of downtown Chicago, Skokie is just one of the neighborhoods that make this city so charming.

At last count, the population of Chicago was 2,700,000.

Hotels in Skokie

Quality accommodations are at your fingertips if you're considering basing yourself in Skokie. There are 2 properties to choose from that are only a stroll from the center. Move fast to book your room of choice!

Look up the deals at the DoubleTree by Hilton Chicago - North Shore Conference Center (9599 Skokie Blvd) and the Rodeway Inn (9333 Skokie Blvd). They're our top picks.

Places to visit in Skokie

Live theater can challenge our expectations and asks us to aspire to be more. Attend a play at North Shore Center for the Performing Arts and open your mind to some big ideas. Need more nearby options? Stop and admire the vast collection of ferns, herbs, trees and bushes at Emily Oaks Nature Center. If you're up for a challenge, try to pronounce their tongue-twisting scientific names! But there's more. The intimacy and mastery of live theater is not to be missed. Get tickets for a performance at Skokie Theatre and experience its magic and charm for yourself!

Where do you fly into for Skokie?

Ready to begin your next great escape? Well, Skokie is approximately 9 miles (14 kilometers) from O'Hare International Airport (ORD).

Frequently asked questions

How much are vacation packages to Skokie?
Travelocity has package deals to Skokie, including flights and hotels, starting from as low as CA $993. With the money you save, you could book some cool tours or maybe add a few extra days to your getaway.
How long should my Skokie vacation be?
Around 3 nights is the average time frame visitors spend in Skokie. But the perfect trip length all comes down to how many treasured memories you want to make. Why not stay a few extra days and uncover some of the lesser-known sights?
Where can I get the best vacation package deals for Skokie?
You can snap up terrific Skokie package deals with Travelocity. Pick from as many as 400 partner airlines and 1,000,000 worldwide properties and turn those travel fantasies into a reality.
Why should I book my Skokie vacation package with Travelocity?
We take the stress out of travel planning. Whether you’re searching for an amazing new place to discover or want to make sure you get the best price on offer, we’ve got your back. Our 24/7 customer care, excellent service and Price Match Guarantee mean you can book with confidence with Travelocity.
Will I save money on my Skokie car rental if I book it with a hotel or flight?
With a Skokie vacation package, you can bundle your car, flight and hotel bookings and save loads. If you’re eager to uncover the best of this wonderful destination, why not head to University of Wisconsin-Madison? This must-see attraction is 177 kilometers from Skokie. With your own wheels, you’ll be there in the blink of an eye.
Which airport is best for Skokie?
O’Hare Intl. Airport (ORD) is 14 kilometers from downtown and is the beginning point for many fun adventures. Alternatively, Midway Intl. Airport (MDW) is 27 kilometers away from central Skokie and Lewis University Airport (LOT) is 56 kilometers away from central Skokie.
What is there to do in Skokie?
There is an undeniable magic as you roam the streets of Skokie. North Shore Center for the Performing Arts and Schaefer’s Wines and Liquors are just a couple of famous sights that make this city such a sought-after destination, so put them on your to-do list.
Where should I stay when visiting Skokie?
The Holiday Inn Chicago North Shore, an IHG Hotel is the first choice of many travelers. Book soon to avoid missing out.

Photos of local treasures

Browse Skokie vacation photos for more inspiration