Skokie Vacation Packages 2026 from $551

Skokie flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Level Chicago – Old Town

Downtown Chicago

$551

per person

Jan 15 - Jan 18

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

$880

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Pendry Chicago

Downtown Chicago

$842

per person

Jan 11 - Jan 17

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Grand Geneva Resort & Spa

$1,207

per person

Jan 18 - Jan 25

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This smoke-free resort features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities.

Trump International Hotel & Tower Chicago

Downtown Chicago

$803

per person

Jan 15 - Jan 18

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Top Skokie hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$123 total

per night

Nov 23 - Nov 24

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.

Free WiFi

Restaurant

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free Cancellation

Reserve now, pay when you stay

$138 total

per night

Nov 9 - Nov 10

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.

Pet friendly

Free WiFi

River Hotel

75 East Wacker Drive Chicago IL

Free Cancellation

Reserve now, pay when you stay

$131 total

per night

Nov 26 - Nov 27

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.

Pet friendly

Free WiFi

The Wade

644 N Lake Shore Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$141 total

per night

Nov 23 - Nov 24

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.

Pool

Pet friendly

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$149 total

per night

Nov 11 - Nov 12

This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.

Pet friendly

Free WiFi

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$158 total

per night

Nov 27 - Nov 28

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

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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.

Stay near popular Skokie attractions

North Shore Center for the Performing Arts

8.0/10 (61 reviews)

Enjoy a stop at North Shore Center for the Performing Arts, an entertaining place to visit in Skokie. Experience the great live music or attend a sporting event in this vibrant area.

See properties

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 $551. 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 110 mi 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 9 mi from downtown and is the beginning point for many fun adventures. Alternatively, Midway Intl. Airport (MDW) is 17 mi away from central Skokie and Lewis University Airport (LOT) is 35 mi 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.