Wildwood Vacations from ￥319,743

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The Latest Wildwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was ￥419,443, price is now ￥319,743 per person
￥319,743
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,503 reviews)
Overall really clean I just wish they had room service, and the TVs had access to Netflix atleast.

Reviewed on Apr 6, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥440,690, price is now ￥329,005 per person
￥329,005
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The room was clean. Very modern hotel. Great service and staff. Great experience overall.

Reviewed on Apr 7, 2026

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was ￥438,748, price is now ￥334,531 per person
￥334,531
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,471 reviews)
Staff was friendly, however I asked to have blankets brought up to room two times (one phone call and one text) and there was no follow through. The room smelled like stale smoke. The pull out bed was awful and you could feels the bedsprings. They also offered to bring coffee to the room and when I requested a time, it was never delivered. I mentioned to from desk and they apologized and had coffee sent to room, however we were ready to check out. They did offer a late check out and staff was friendly. We were dissapointed that we couldn't pay cash, although that wouldn't have been a deal breaker. Rooms could use a little updating.

Reviewed on Apr 4, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was ￥432,342, price is now ￥345,187 per person
￥345,187
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.

Reviewed on Apr 6, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥399,386, price is now ￥320,874 per person
￥320,874
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Great experience and friendly staff

Reviewed on Apr 6, 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

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 ￥319,743. 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

Wrigley Field

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

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

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

￥4,285
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,348
per adult
94% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,427
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.