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Winnetka flight + hotel packages

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Super 8 by Wyndham Aurora/Naperville Area

Super 8 by Wyndham Aurora/Naperville Area

2 out of 5
Fox Valley
Price was CA $1,165, price is now CA $717 per person
CA $717
per person
Sep 17 - Sep 19
found 13 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Book a stay at this business-friendly motel in Aurora. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Chasers Laser Tag and Moser Tower and Millennium Carillon are located nearby.
Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Price was CA $1,260, price is now CA $780 per person
CA $780
per person
Sep 16 - Sep 19
found 13 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Allstate Arena and Milwaukee Avenue are located nearby.
Luxe Inn and Suites

Luxe Inn and Suites

2.5 out of 5
Price was CA $1,204, price is now CA $748 per person
CA $748
per person
Sep 17 - Sep 19
found 13 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Stay at this motel in Dolton. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Veterans Memorial Park and River Oaks Center are located nearby.
Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

2.5 out of 5
Ashburn
Price was CA $1,272, price is now CA $793 per person
CA $793
per person
Sep 16 - Sep 19
found 13 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and room service. Popular attractions SeatGeek Stadium and Wintrust Sports Complex are located nearby.
Motel 6 Libertyville, IL

Motel 6 Libertyville, IL

2 out of 5
Price was CA $1,197, price is now CA $747 per person
CA $747
per person
Sep 17 - Sep 19
found 13 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Book a stay at this business-friendly motel in Libertyville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Six Flags Great America and Gurnee Mills are located nearby.

Top Winnetka 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 $173 per night
CA $173
CA $205 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). 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
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $217 per night
CA $217
CA $306 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Free WiFi
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $260 per night
CA $260
CA $309 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Pet-friendly
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Free cancellation
Reserve now, pay when you stay
The price is CA $240 per night
CA $240
CA $273 total
Aug 3 - Aug 4
includes taxes & fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
Free airport shuttle
Pet-friendly
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $204 per night
CA $204
CA $283 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Breakfast included
Free WiFi
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $311 per night
CA $311
CA $366 total
Jul 4 - Jul 5
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fashion Outlets of Chicago and Rosemont Theatre are located nearby.
Free airport shuttle
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.

Stay near popular Winnetka attractions

Chocolate Box

Enjoy a stop at Chocolate Box, an entertaining place to visit in Winnetka. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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Winnetka Vacations

A memorable, hassle-free adventure begins with getting to know a bit of information about your destination. It's time to discover the basic details about Winnetka!

Around 16 miles (26 kilometers) northwest of central Chicago, Winnetka is one of the neighborhoods that make this city so charming.

Ready to rub shoulders with the locals? 2,700,000 people live in Chicago.

Places to visit in Winnetka

Everyone knows that being around animals can help reduce stress. So, if always being on the move is tiring you out, why not make your way to Wagner Farm? But that's not all there is. Theater can challenge our world views and asks us to aspire to higher things. Catch a play at Writers Theatre and open your mind to some new ideas.

Where do you fly into for Winnetka?

Flying into O'Hare International Airport (ORD)? Get through security, step out of the terminal and you'll be 12 miles (19 kilometers) southwest from the heart of Winnetka.

Frequently asked questions

How much are vacation packages to Winnetka?
With vacation packages on offer for just CA $717, it's not necessary to max out the credit card for your getaway to Winnetka. Travelocity is here to help. Combine experiences, hotels and flights into a package and land some fantastic discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Winnetka?
No matter your travel style, Travelocity can help you get your hands on an unbeatable Winnetka package deal. The only thing you have to do is pick and choose between our 400 partner airlines and 1,000,000 properties across the globe.
Why should I book my Winnetka vacation bundle with Travelocity?
From amazing destinations to thrilling experiences, we have everything you need to appease your wanderlust. Our 24/7 customer care will also make sure you're taken care of while you're on your getaway. And don't panic if you notice a lower price on your booking, we'll match it. That's our Price Match Guarantee.
Can I save on my Winnetka car rental if I book it with my hotel or flight?
Bundling your flight, car and hotel into a Winnetka vacation package is a great way to land the best prices. Plus, having your own rental car gives you total freedom to make your way to all those big-name sights you're eager to explore. Situated 177 kilometers from Winnetka, University of Wisconsin-Madison is one attraction that should be on your can't-miss list. Put together a driving playlist and make a day trip of it.
Which airport is best for Winnetka?
Many people choose to fly into O'Hare Intl. Airport (ORD), 21 kilometers southwest of downtown Winnetka. Others prefer Midway Intl. Airport (MDW) (32 kilometers away from central Winnetka) or General Mitchell Intl. Airport (MKE) (97 kilometers away from central Winnetka).
What is there to do in Winnetka?
Elder Lane Beach is one of the memorable sights that make Winnetka a popular place to visit. But allow some extra time to explore the city's lesser-known attractions too. This is often where the best vacation memories are made.
Where should I stay when visiting Winnetka?
Many people opt to stay at the North Shore 4 bedroom home near New Trier Schools. It's sure to be a good base for your Winnetka getaway.

Photos of local treasures

Browse Winnetka vacation photos for more inspiration

A suburban street with a stone house, a tree, and a clear sky.

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