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 Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,126, price is now CA $804 per person
CA $804
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (126 reviews)
All the cuteness of a boutique hotel, with all the Marriott amenities and a great staff too! This will be my #1 pick for Chicago hotels from now on

Reviewed on Jul 1, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,670, price is now CA $1,118 per person
CA $1,118
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Great property in the heart of the city

Reviewed on Jul 1, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,250, price is now CA $872 per person
CA $872
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar.

Reviewed on Jul 1, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,393, price is now CA $1,698 per person
CA $1,698
per person
Sep 1 - Sep 6
found 23 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on Jun 26, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,516, price is now CA $1,087 per person
CA $1,087
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Excellente

Reviewed on Jul 1, 2026

Ready to book your vacation to Willow Springs?

 

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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 $173 per night from Jul 6 to Jul 7
CA $173
CA $205 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very good! (10,189 reviews)
"Lugar limpio, buenas ubicación"

Reviewed on Jul 1, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $306 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,828 reviews)
"Very nice hotel. Great location, nice sized rooms."

Reviewed on Jul 2, 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Jul 9 to Jul 10
CA $225
CA $267 total
Jul 9 - Jul 10
includes taxes & fees
9/10 Wonderful! (4,478 reviews)
"R"

Reviewed on Jul 2, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,500 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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What to do in Willow Springs

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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 all activities in Willow Springs

Frequently asked questions

How much does a Willow Springs vacation package cost?
Offering great value package deals from CA $804 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.

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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.