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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
Great location awesome staff...

Reviewed on Aug. 4, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
I booked a room with the water view, when I checked in I asked before I get the key, Is it a water view. They told me it is. I show up in my room and it’s not the room I booked. I called the front desk and they’re telling me we apologize all of the rooms are booked with the water view. They also said booking a water view room doesn’t guarantee a water view room even though I paid extra for a water view room! Never going to stay there again for sure.

Reviewed on Aug. 3, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,922 reviews)
We spent 4 nights and had no major complaints. I don't understand why there was an additional mandatory destination fee for normal amenities that we did not ask for or use.

Reviewed on Aug. 1, 2025

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Willow Springs 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 $185 per night from Aug 5 to Aug 6
CA $185
CA $217 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,940 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on Aug. 1, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 21 to Aug 22
CA $239
CA $315 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,816 reviews)
"Third stay at the Palmer House. We'll be back."

Reviewed on Jul. 31, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $201 per night from Aug 24 to Aug 25
CA $201
CA $236 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,335 reviews)
"Thanks beautiful place"

Reviewed on Aug. 3, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,690 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
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

CA $41
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

CA $62
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Willow Springs

Frequently asked questions

How much does a Willow Springs vacation package cost?
Offering great value package deals from CA $677 on Expedia, you'll be pleasantly surprised at how much a vacation to Willow Springs costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Willow Springs?
If you're hoping to snag a cheap Willow Springs vacation package, consider planning a trip in January, February and November. You'll usually find lower rates on flights and accommodations during these quieter months — perfect for a budget-friendly break.
How many days is enough for Willow Springs?
Allow at least 7 days for your Willow Springs vacation if you're hoping to immerse yourself in all that makes this destination unique. Stroll around popular areas, including Clearing and Indian Head Park. Then make a beeline for top attractions like Galloping Ghost and Moraine Valley Community College Fine and Performing Arts Centre. With a well-planned itinerary, you can keep busy with room for some rest time too. Want to travel outside of Willow Springs? Consider squeezing in a day trip or two.
How to find the best Willow Springs package deals?
Use Expedia's handy filters to help you find some fabulous Willow Springs package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Willow Springs package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Willow Springs vacation as a package?
You can enjoy significant savings on your Willow Springs break by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Willow Springs?
If you're planning a spur-of-the-moment Willow Springs adventure, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Willow Springs?

  1. Pick your travel dates: The things you'd like to do in Willow Springs and your preferred season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will probably be the largest expense during your trip to Willow Springs.
  3. Decide how many days away: Start by making a list of all the attractions you'd like to get to in Willow Springs. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the perfect Willow Springs vacation package for you.

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