Wildwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

Your Wildwood Vacation

When you book a Wildwood vacation package, it's all about enjoying your escape to the fullest. Uncover the best things about this fun-filled city knowing that all your travel needs have been organized in advance. Fill your days with visits to Lake County Fairgrounds, College of Lake County and Jones Island Beach, some of the things you shouldn't miss during your trip to Wildwood. Check out Expedia's wide range of travel options and begin planning your dream vacation to Wildwood today.

Top Holiday Package Deals in Wildwood

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
West Lawn
Price was CA $1,014, price is now CA $772 per person
CA $772
per person
Jun 5 - Jun 8
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.4/10 Very Good! (1,014 reviews)
Fast, friendly, outstanding service

Reviewed on Mar 18, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,617, price is now CA $1,106 per person
CA $1,106
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.

Reviewed on Mar 20, 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 $1,419, price is now CA $995 per person
CA $995
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great location, views, & amenities.

Reviewed on Mar 20, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,667, price is now CA $1,255 per person
CA $1,255
per person
Apr 28 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Truly one of our favorite stays! The staff makes you feel at home & are super accommodating. I will stay here every time! The bellman Michael is quite literally the best ever!! He made our stay so wonderful and special!

Reviewed on Mar 16, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,029, price is now CA $792 per person
CA $792
per person
May 1 - May 3
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
Hot tubs was the best part!! Super hot water

Reviewed on Mar 17, 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 showing a city

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

Comfort Suites Grayslake near Libertyville North

Comfort Suites Grayslake near Libertyville North

2.5 out of 5
1775 East Belvidere Road Grayslake IL
Fully refundable
The price is CA $129 per night from Mar 30 to Mar 31
CA $129
CA $143 total
Mar 30 - Mar 31
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Room was okay

Reviewed on Mar 19, 2026

Comfort Suites Grayslake near Libertyville North
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
1750 Lake Cook Rd Deerfield IL
The price is CA $159 per night from Mar 22 to Mar 23
CA $159
CA $180 total
Mar 22 - Mar 23
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
This particular Hyatt Regency is in a terrible need of complete renovation. The room I stayed in had HVAC issues and plumbing problems. Tacky old decor makes a place very unpleasant looking. There are better options in the area.

Reviewed on Mar 12, 2026

Hyatt Regency Deerfield
Embassy Suites by Hilton Chicago North Shore Deerfield

Embassy Suites by Hilton Chicago North Shore Deerfield

4 out of 5
1445 Lake Cook Rd Deerfield IL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Apr 2 to Apr 3
CA $178
CA $202 total
Apr 2 - Apr 3
includes taxes & fees
8.8/10 Excellent! (1,289 reviews)
Clean room

Reviewed on Mar 21, 2026

Embassy Suites by Hilton Chicago North Shore Deerfield
See all 809 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?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Wildwood from just CA $772. And the more you bundle, the more dollars you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Wildwood?
Browse and lock in everything all in one place with our Wildwood vacation packages. You'll discover bargains on hotels, flights and more that'll keep your wallet happy and adventurous side satisfied. And, with more than 550 airlines and 1,000,000 hotel options throughout the world to select from, you'll have the flexibility to mix and match your own way.
Where should I stay in Wildwood?
Stay where the action happens. Many travelers like to book hotels within easy reach of top sights, like Lake County Fairgrounds, College of Lake County and University Center of Lake County.
How far in advance should I book my Wildwood vacation?
You'll be rewarded with the widest variety at the lowest prices by booking your Wildwood vacation early. Airlines usually publish flight tickets anywhere up to 12 months in advance, so start locking things in ASAP. Having said that, Expedia is committed to giving you the best deals around, so it's never a bad time to book your dream vacation!
What does an Expedia Wildwood travel package include?
It depends on what kind of escape you want to have. Wildwood travel deals can include car rentals, hotels and flights. You can mix and match to create the package that works for you! You can also add on experiences and activities after you've booked to land even bigger discounts.
What should I know before booking a Wildwood travel package?
Our prices are already low. However, you'll pick up even more savings if you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and lots of choice.
Can I choose my airline with a Wildwood Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You're the boss! We have more than 550 partner airlines around the world, so you have lots of choice when putting together your Wildwood adventure.
If I'm not able to travel, can I cancel my Wildwood vacation package?
It is possible to cancel your Wildwood booking if your plans have changed. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Discover the most popular places to visit in Wildwood

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

Wrigley Field

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

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
Navy Pier featuring a sunset and rides

Navy Pier

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 $36
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
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.