Waukegan Vacations from ¥311,696

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The Latest Waukegan Vacation Packages

Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
¥311,696
per person
Nov 9 - Nov 13
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,352 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥375,400
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥374,042
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥398,572
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Clean. On site laundry was awesome.

Reviewed on Oct 6, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥530,538
per person
Nov 9 - Nov 13
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)

Find the Best Waukegan Vacation Packages

Waukegan Hotel Deals

Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

1440 S White Oak Dr Waukegan IL
Fully refundableReserve now, pay when you stay
¥16,748
¥18,754 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (1,726 reviews)
"I have stayed at this hotel three times, each time for five days. It’s always been clean, the staff is always been amazing and responsive, and it’s in a great location. Highly recommend."

Reviewed on Oct 7, 2026

Sonesta ES Suites Chicago Waukegan Gurnee
Courtyard Chicago Waukegan Gurnee

Courtyard Chicago Waukegan Gurnee

3800 Northpoint Blvd Waukegan IL
Fully refundableReserve now, pay when you stay
¥20,011
¥22,409 total
Oct 23 - Oct 24
includes taxes & fees
Courtyard Chicago Waukegan Gurnee
Days Inn by Wyndham Waukegan

Days Inn by Wyndham Waukegan

630 N Green Bay Road Waukegan IL
Fully refundableReserve now, pay when you stay
¥12,758
¥14,286 total
Nov 1 - Nov 2
includes taxes & fees
Days Inn by Wyndham Waukegan
See all 771 properties in Waukegan
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.

Stay near popular Waukegan attractions

A waterfront with a dock, buildings, and a large tree reflecting in calm water.

Waukegan Harbor

8.2/10 (152 reviews)
Waukegan Harbor offers over 1,000 slips for vessels along Lake Michigan's scenic shoreline. Boaters can enjoy the full-service marina with dining options and access to the adjacent beach and arts district.
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A sandy beach with a curved pier extending into the sea, surrounded by calm waters and a clear sky.

North Beach

8.2/10 (61 reviews)
North Beach offers a mile of pristine Lake Michigan shoreline with rare natural sand dunes. Enjoy summer concerts at Stiner Pavilion or take a short walk to downtown Waukegan's vibrant arts district.
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Genesee Theater

7.8/10 (145 reviews)
This 1927 movie palace captivates with its restored grandeur and stunning Baccarat crystal chandelier. Experience world-class performances in a venue where historic elegance meets perfect acoustics.
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The Temporary by American Place

8.0/10 (7 reviews)
Why not roll the dice with a visit to The Temporary by American Place during your visit to Waukegan? Stroll along the lakeside or visit the shops in this family-friendly area.
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Waukegan SportsPark

7.2/10 (88 reviews)
This premier sports complex features soccer fields and lighted softball fields for regional tournaments. Families can enjoy the playground and splash pad while watching competitive matches in this well-equipped venue.
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American Place Casino

10.0/10 (1 review)
Why not try your luck with a visit to American Place Casino during your travels in Waukegan? Stroll along the lakeside or visit the shops in this family-friendly area.
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Waukegan BMX Track

6.6/10 (48 reviews)
This local BMX track offers a structured environment for riders of all skill levels to practice and compete. Visitors can watch exciting races from designated viewing areas during spring through fall.
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Bonnie Brook Golf Course

6.6/10 (49 reviews)
This classic James Foulis-designed course offers rolling terrain and tree-lined fairways along a meandering creek. Experience championship golf in a welcoming atmosphere with country-club conditions on a public course.
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What to do in Waukegan

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

¥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

¥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Waukegan

Frequently asked questions

How much does a Waukegan vacation package cost?
You can snap up a vacation package to this top destination from ¥311,696 on Expedia. However, how much your vacation to Waukegan costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Waukegan?
You can generally find lower prices and better availability in February, March and December. Take a look at our cheap Waukegan vacation packages and you could land some great off-season discounts.
How many days is enough for Waukegan?
With a well-planned itinerary, you can easily visit the top Waukegan sights in a handful of days. But if you prefer to discover lesser-known spots or go on day trips, think about booking your Waukegan vacation for longer.
Is it worth booking a vacation package to Waukegan?
Known for its history, culture and a host of other highlights, you can be assured Waukegan is a good vacation destination. Some of the most popular attractions to put on your to-do list? Don't miss Genesee Theater and Bonnie Brook Golf Course during your Waukegan vacation.
How to find the best Waukegan package deals?
Landing a cheap Waukegan package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Waukegan package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Waukegan vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Waukegan getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Waukegan?
If you've got your Waukegan travel dates locked in, book early to snap up some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Waukegan?
  1. Choose when to go: Check your diary and get your bags packed. Your favorite season and the type of activities on offer will also help you decide when to vacation in Waukegan.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Waukegan.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you want to get to in Waukegan. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Waukegan vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.