Wildwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Wildwood

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,930, price is now CA $1,296 per person
CA $1,296
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $5,407, price is now CA $2,968 per person
CA $2,968
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.

Reviewed on May 16, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,256, price is now CA $1,425 per person
CA $1,425
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.

Reviewed on May 18, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $4,447, price is now CA $2,861 per person
CA $2,861
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
The Sable was beautiful and peaceful. We enjoyed our stay and would definitely come back. Thanks for the great customer service.

Reviewed on May 17, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,893, price is now CA $1,935 per person
CA $1,935
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (984 reviews)
Easy and comfortable

Reviewed on May 18, 2026

Where to stay in Wildwood

Find the best Wildwood areas and neighborhoods for the activities you enjoy most. Learn more about Wildwood
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Wildwood 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 $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,150 reviews)
"Always stay here when I’m trying to save money great location and price"

Reviewed on May 17, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from May 25 to May 26
CA $239
CA $324 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,176 reviews)
"The hotel was clean, staff was friendly and very helpful. My room was clean and the breakfast buffet was phenomenal. I recommend this hotel and will be a returning customer."

Reviewed on May 18, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,429 reviews)
"I paid for room almost $600 but Expedia didn’t send me breakfast."

Reviewed on May 18, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,812 properties in Wildwood
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Wildwood vacation package cost?
Our Wildwood packages, which start from just CA $1,296, are the easiest way to save big bucks. Pick and choose your preferred flights, hotels and rental cars to create your perfect itinerary.
How do I get a cheap travel package to Wildwood?
If you love amazing deals, combine your bookings into a Wildwood vacation package. Whether you're searching for flights, hotels, rental cars or tours, you can book everything in one place. You'll have lots of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 properties around the world to choose from. Fly with who you prefer, book a room where you like and save precious money — now that's the ideal vacation!
Where should I stay in Wildwood?
Book a hotel nice and close to Lincoln Park, one of this area's biggest attractions. It's the perfect spot if you're an eager sightseer.
What are the top hotels in Wildwood?
When it comes to comfortable and convenient places to stay in Wildwood, you can't go past Edgebrook Motel. Have a look at our deals and score a great price.
How far in advance should I book my Wildwood vacation?
Travelers are generally able to look up international airfares on Expedia up to 12 months prior to departure. Booking late? With a bit of luck, it's still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Wildwood travel package include?
Packages include flights, rental cars and hotels, but you can mix and match them to create your perfect Wildwood escape. You can also add on experiences and activities once you've made your booking. You're in charge! When you bundle your bookings with Expedia, you'll get access to discounts you won't find elsewhere.
What should I know before booking a Wildwood travel package?
Whether it's relaxation or adventure you're after, a Wildwood vacation package lets you organize your escape your way. Plus, you'll score great discounts just for combining your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Wildwood Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the flexibility to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Wildwood vacation package?
Whether it's your hotel or flight, you can cancel and rebook it. Locked in your Wildwood vacation package in the last 24 hours? You may be able to make any changes for free. If it's been longer than that, you may incur a charge from your hotel, airline or car rental company. For more information, head to our Customer Service Portal. We'll help you each step of the way.

Discover the most popular places to visit in Wildwood

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.