South Holland Vacation Packages

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Your South Holland Vacation

With all your travel needs organized before you head off, our South Holland vacation packages let you simply focus on having fun! One neighborhood to consider staying in this vibrant city is South Deering, which is great for golfing and nature. A trip to South Holland is an excellent opportunity to take in the sights. Be sure to look around renowned attractions like Coyote Run Golf Course, River Oaks Center and Ravisloe Country Club. Stop daydreaming and start adventuring. Explore the broad range of options on Expedia today and put your South Holland vacation plans into action!

Top South Holland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Naperville/Warrenville

Hilton Garden Inn Naperville/Warrenville

3 out of 5
Price was CA $1,243, price is now CA $845 per person
CA $845
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Minor issues: The room was fairly clean. There was some dust in the bathroom, furniture and candy found on the floor under the table from the previous guests. The room was cleaned during our stay, but they did not restock our toilet paper.

Reviewed on May 5, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,609, price is now CA $1,589 per person
CA $1,589
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on May 22, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,753, price is now CA $1,209 per person
CA $1,209
per person
Aug 7 - Aug 10
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.

Reviewed on May 18, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,102, price is now CA $1,491 per person
CA $1,491
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,017 reviews)
I don’t have any complaints about the property! I will always stay here when I’m in Chicago! The room was beyond clean, the view was amazing especially at night! Parking was safe and secure at the property.

Reviewed on May 27, 2026

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was CA $1,816, price is now CA $1,293 per person
CA $1,293
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,005 reviews)
I had a very nice view of the lake from my room. The air conditioning was a little loud but other than that a pleasant stay.

Reviewed on May 27, 2026

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South Holland Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $281 per night from Jun 3 to Jun 4
CA $281
CA $334 total
Jun 3 - Jun 4
includes taxes & fees
8/10 Very Good! (10,149 reviews)
"Hotel is pretty "okay" if you are going for business, but our experience was not nice. The Air Conditioner wasn't working on a 65-80 degree outside, I told the front desk if they can help or make a room change but the solution was to give me a floor fan, not the type of help I was hoping and did ..."

Reviewed on May 27, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $328 per night from Jun 14 to Jun 15
CA $328
CA $390 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (5,196 reviews)
"had an excellent stay.... very nice hotel for the price. Great location. Great room."

Reviewed on May 27, 2026

River Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
The price is CA $248 per night from Jun 28 to Jun 29
CA $248
CA $295 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,346 reviews)
"It is not what it indicates in the description of the hotel everything is far away the photos that you show are from a different place as well as the distance all my stay there was very frustrating"

Reviewed on May 28, 2026

Holiday Inn Chicago Dwtn - The Mart by IHG
See all 2,389 properties in South Holland
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
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Family Vacations

Discover the most popular places to visit in South Holland

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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

What to do in South Holland

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
See all activities in South Holland

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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.