Willow Springs Vacation Packages

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Your Willow Springs Vacation

With all your travel plans organized before you go, our Willow Springs vacation packages mean you can simply focus on having a good time! One place to base yourself in this vibrant city is Little Village, which is great for cafes and shopping. If your trip to Willow Springs includes some sightseeing, drop by popular attractions like SeatGeek Stadium, Chicago Ridge Shopping Mall and Burr Ridge Village Center. Whatever your travel plans or the size of your budget, organizing a tailored Willow Springs vacation is a cinch with Expedia.

Top Willow Springs Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,375, price is now CA $820 per person
CA $820
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $4,139, price is now CA $2,373 per person
CA $2,373
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,012, price is now CA $1,767 per person
CA $1,767
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $2,135, price is now CA $1,256 per person
CA $1,256
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Excellent staff very friendly

Reviewed on Aug. 29, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,066, price is now CA $1,229 per person
CA $1,229
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on Aug. 29, 2025

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Willow Springs Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Sep 4 to Sep 5
CA $207
CA $244 total
Sep 4 - Sep 5
includes taxes & fees
8.2/10 Very Good! (1,226 reviews)
"It was very close to navy pier where it was just a 10 min way. And had a great view from our room. Facing the lake"

Reviewed on Aug. 27, 2025

The Wade
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 $194 per night from Sep 1 to Sep 2
CA $194
CA $228 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (9,045 reviews)
"Very convenient to South Loop sites!"

Reviewed on Aug. 26, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is CA $231 per night from Sep 3 to Sep 4
CA $231
CA $271 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."

Reviewed on Aug. 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,811 properties in Willow Springs
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.
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Discover the most popular places to visit in Willow Springs

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

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

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Willow Springs

River tour boat in Chicago

Architecture River Tour

CA $57
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

CA $56
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

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Willow Springs
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.