Wildwood Vacations from ￥262,424
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Wildwood Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥295,616
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Place in the heart of the city. Accessable to all establishment. Staffs are great. Feels home
Reviewed on Sep 19, 2026
The Peninsula Chicago
Downtown Chicago
￥375,078
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
We had a spectacular stay! The service was truly first-class, and every member of the staff was incredibly friendly and welcoming. The restaurant servers were excellent, and the live music during lunch was one of the highlights of our stay.
Everything was spotless, and we were made to feel especially welcome while celebrating our anniversary. All of our special requests were handled perfectly, which made the experience even more memorable.
We would definitely stay here again the next time we’re in Chicago. Highly recommended!
Reviewed on Sep 20, 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
4 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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Wildwood Hotel Deals
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road Grayslake IL
Fully refundable
￥14,825
￥16,453 total
Oct 11 - Oct 12
includes taxes & fees
Hyatt Regency Deerfield
1750 Lake Cook Rd Deerfield IL
Fully refundableReserve now, pay when you stay
￥21,179
￥23,927 total
Oct 4 - Oct 5
includes taxes & fees
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Fully refundableReserve now, pay when you stay
￥17,109
￥18,988 total
Oct 4 - Oct 5
includes taxes & fees
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.
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 ￥262,424. 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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,453
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,886
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.