Waukegan Holidays
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Top Flight + Hotel Deals in Waukegan
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
Price was €944, price is now €565 per person
€565
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
I wish that all the staff was more accommodating! some of them were some were not!
Reviewed on 6 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €1,201, price is now €678 per person
€678
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend
Reviewed on 7 Oct 2025
Swissotel - Chicago
Downtown Chicago
Price was €1,206, price is now €694 per person
€694
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice
Reviewed on 9 Oct 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,040, price is now €643 per person
€643
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!
Reviewed on 7 Oct 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,089, price is now €682 per person
€682
per person
10 Nov - 16 Nov
found 1 day ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
Absolutely loved this place.... views were great, staff was great, atmosphere was great! One of my most favorite places to stay.
Reviewed on 8 Oct 2025
Top hotels in Waukegan
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr, Waukegan, IL
Fully refundableReserve now, pay when you stay
The price is €106 per night from 19 Oct to 20 Oct
€106
19 Oct - 20 Oct
includes taxes & fees
8.8/10 Excellent! (1,425 reviews)
"We stayed here for my child’s bootcamp graduation. Overall our stay was good. It was pretty quiet until one of the families who was staying a room or two down from ours started arguing really really loud that we thought cops would be called but I guess they sorted it out coz it stopped. I can’t rate ..."
Reviewed on 4 Oct 2025
Red Roof Inn Gurnee - Waukegan
3031 Belvidere Rd, Waukegan, IL
Fully refundableReserve now, pay when you stay
The price is €74 per night from 12 Oct to 13 Oct
€74
12 Oct - 13 Oct
includes taxes & fees
7/10 Good! (1,003 reviews)
"It’s weird people around in the parking lot."
Reviewed on 2 Oct 2025
Courtyard Chicago Waukegan Gurnee
3800 Northpoint Blvd, Waukegan, IL
Fully refundableReserve now, pay when you stay
The price is €140 per night from 19 Oct to 20 Oct
€140
19 Oct - 20 Oct
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"The bedding didn't look clean. There were makeup stains and I don't wear makeup."
Reviewed on 30 Sept 2025
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.
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Waukegan
Skydeck - Willis Tower Admission
€38
per adult
100% of travellers recommend
Chicago By Night River & Lake Cruise
€38
per adult
96% of travellers recommend
Chicago Sightseeing River and Lake Cruise
€38
per adult
100% of travellers recommend
More trip options
Expedia's Latest Trends
Hotels
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Flights
Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
