Waukegan Holidays

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Top Flight + Hotel Deals in Waukegan

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
€698
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€1,947
per person
8 Oct - 13 Oct
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
€872
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
€1,449
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Very dirty

Reviewed on 22 Aug 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
€2,017
per person
8 Oct - 13 Oct
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (2,348 reviews)

Top hotels in Waukegan

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
€113
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (1,676 reviews)
"Great experience with staff and room was clean, however the hot tub wasn’t working and there were some homeless ppl who were in and out of the building and the doors weren’t always locking to get into the building which made it a bit more worrisome for my family and I. Other than that the place wasn’t ..."

Reviewed on 22 Aug 2026

Sonesta ES Suites 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
€86
23 Aug - 24 Aug
includes taxes & fees
Days Inn by Wyndham Waukegan
Courtyard Chicago Waukegan Gurnee

Courtyard Chicago Waukegan Gurnee

3800 Northpoint Blvd Waukegan IL
Fully refundableReserve now, pay when you stay
€133
30 Aug - 31 Aug
includes taxes & fees
Courtyard Chicago Waukegan Gurnee
See all 760 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 Harbour 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 city centre Waukegan's vibrant arts district.
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Genesee Theater

7.8/10 (145 reviews)
This 1927 film 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 time in 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 football 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 visit to 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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Bowlero Waukegan

Bowlero Waukegan blends modern bowling lanes with arcade games in a vibrant setting. Enjoy cosmic bowling with signature cocktails and shareable dishes while challenging friends to both classic and contemporary games.
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What to do in Waukegan

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Waukegan

Frequently asked questions

How much does a Waukegan holiday package cost?
You can snap up a holiday package to this top destination from €698 on Expedia. However, how much your holiday 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 holiday 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 holiday for longer.
Is it worth booking a holiday package to Waukegan?
Known for its history, culture and a host of other highlights, you can be assured Waukegan is a good holiday destination. Some of the most popular attractions to put on your to-do list? Don't miss Genesee Theatre and Bonnie Brook Golf Course during your Waukegan holiday.
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," "Traveller 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Waukegan holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and accommodation 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 holiday 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 travelling on a whim.
How to plan a trip to Waukegan?
  1. Choose when to go: Check your diary and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to holiday 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 accommodation 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 personalised Waukegan holiday package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.