Wildwood Vacations from $312

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to $1,045 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.

The Latest Wildwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $560, price is now $312 per person
$312
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $738, price is now $379 per person
$379
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
We loved the Pendry!

Reviewed on Oct 27, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $805, price is now $422 per person
$422
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Excellent stay. The hotel staff is very courteous and helpful, and the location is great!

Reviewed on Oct 28, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $828, price is now $454 per person
$454
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Easy check-in, friendly staff, beautiful building with nice amenities.

Reviewed on Oct 27, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $883, price is now $517 per person
$517
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
I had the pleasure of staying with this hotel during a recent work trip. They were as lovely as can be, the hotel and room were very clean, and the included breakfast buffet exceeded all my expectations. The area had a lot to see and was easily walkable. Looking forward to my next Chicago trip so I can stay here again.

Reviewed on Oct 28, 2025

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

Motel 6 Prospect Heights, IL

Motel 6 Prospect Heights, IL

2 out of 5
540 N Milwaukee Ave, Prospect Heights, IL
Fully refundable
$45 nightly
The price is $50 total per night from Nov 9 to Nov 10
$50 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (1,466 reviews)
Clean and tidy room. Basic but clean and nothing to complain about in the room. I felt the location of the hotel was a bit sketchy.

Reviewed on Oct 22, 2025

Motel 6 Prospect Heights, IL
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
1750 Lake Cook Rd, Deerfield, IL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $133 total per night from Nov 14 to Nov 15
$133 total
Nov 14 - Nov 15
Total with taxes and fees
8.4/10 Very Good! (1,015 reviews)
We ove staying at this hotel.

Reviewed on Oct 27, 2025

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
$138 nightly
The price is $157 total per night from Nov 4 to Nov 5
$157 total
Nov 4 - Nov 5
Total with taxes and fees
8.8/10 Excellent! (1,236 reviews)
It was really a nice overall experience from the accommodations to the delicious breakfast.

Reviewed on Oct 24, 2025

Embassy Suites by Hilton Chicago North Shore Deerfield
See all 727 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Wildwood

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

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

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.