Wildwood Vacations from $394

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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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was $907, price is now $394 per person
$394
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The staff were so welcoming! They knew it was our anniversary and we got showered with little nice surprises. Thank you so much for making our stay so memorable and meaningful. Our room was perfect, the lobby and the bar/lounge were beautiful and again the staff were great. Location is within 15 minute walk to every thing. We will definitely be back!

Reviewed on Aug 31, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,009, price is now $522 per person
$522
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,007 reviews)
This was by far the BEST Hotel!!!

Reviewed on Sep 1, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $786, price is now $408 per person
$408
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Had a billing problem and staff quickly resolved it.

Reviewed on Aug 31, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $965, price is now $513 per person
$513
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Good location. Walkable to sites and shopping. Front desk staff not very nice and not personable. Buffet breakfast was not appetizing. Only good thing was the fresh fruit.

Reviewed on Aug 31, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $957, price is now $511 per person
$511
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug 27, 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

Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
1750 Lake Cook Rd, Deerfield, IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $134 total per night from Sep 14 to Sep 15
$134 total
Sep 14 - Sep 15
Total with taxes and fees
8.4/10 Very Good! (988 reviews)
"Nice staff! Clean and cozy room."

Reviewed on Aug 28, 2025

Hyatt Regency Deerfield
Motel 6 Prospect Heights, IL

Motel 6 Prospect Heights, IL

2 out of 5
540 N Milwaukee Ave, Prospect Heights, IL
Fully refundableReserve now, pay when you stay
$55 nightly
The price is $62 total per night from Sep 14 to Sep 15
$62 total
Sep 14 - Sep 15
Total with taxes and fees
Motel 6 Prospect Heights, IL
Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

3 out of 5
1440 S White Oak Dr, Waukegan, IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Sep 21 to Sep 22
$123 total
Sep 21 - Sep 22
Total with taxes and fees
Sonesta ES Suites Chicago Waukegan Gurnee
See all 677 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

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

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

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.