Willow Springs Holidays

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    Save up to €900 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Flight + Hotel Deals in Willow Springs

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
€693
per person
26 Nov - 29 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
€1,032
per person
26 Nov - 29 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Loved the great upgrade in room and the mini bar selection s

Reviewed on 25 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€824
per person
26 Nov - 29 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago
€1,850
per person
27 Nov - 3 Dec
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9/10 Wonderful! (1,123 reviews)
Stayed with kids, they loved the pool…gym looked well equipped. Good location, walkable or short uber ride to main attractions. Food in the restaurant was great but limited menu, seemed a bit overpriced for the place. The hotel is right next to a hospital, even from our top 17th floor we heard plenty of ambulances throughout our 4 day stay.

Reviewed on 25 Sept 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
€1,575
per person
27 Nov - 3 Dec
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (2,401 reviews)
The hotel was nice! Every employee I encountered was nice, friendly, and helpful.

Reviewed on 25 Sept 2026

Top hotels in Willow Springs

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
€194
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,443 reviews)
"Everything was rough have to leave early"

Reviewed on 26 Sept 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€168
26 Oct - 27 Oct
includes taxes & fees
8/10 Very good! (10,224 reviews)
"Terrible male and female bar staff! Don’t interact with customers, arguing about cups, don’t ask customer if they want a drink or to order food! They are two miserable old men"

Reviewed on 25 Sept 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€168
26 Oct - 27 Oct
includes taxes & fees
8/10 Very good! (2,347 reviews)
"The staff aren’t very friendly and the elevators are annoyingly slow. The buffet needs attention, eggs were cold, they were out of coffee cups. When the cups came out, they were dirty. Their system was down so you had to go back to the front desk, wait in line for a breakfast coupon then go back ..."

Reviewed on 26 Sept 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,661 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.

What to do in Willow Springs

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

€24
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Willow Springs

Frequently asked questions

How much does a Willow Springs holiday package cost?
You can snap up a holiday package to this top destination from €693 on Expedia. However, how much your holiday to Willow Springs costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Willow Springs?
If you're hoping to snag a cheap Willow Springs holiday package, consider planning a trip in January, February and November. You'll typically find better rates on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Willow Springs?
With a well-planned itinerary, you can easily tick off the most popular Willow Springs sights in a few days. But if you'd like to explore off the beaten track or take day trips, consider booking your Willow Springs holiday for longer.
How to find the best Willow Springs package deals?
Use Expedia's filters to find some great Willow Springs package deals. When you begin 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 browse for Willow Springs package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Willow Springs holiday as a package?
You can enjoy significant savings on your next Willow Springs getaway by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to view the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Willow Springs?
If you're planning a spur-of-the-moment Willow Springs holiday, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Willow Springs?
  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Willow Springs.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and food to flights and experiences. Your accommodation will likely be the largest expense during your trip to Willow Springs.
  3. Decide how many days away: Start by making a list of all the activities and attractions you'd like to experience in Willow Springs. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your airfare and accommodation: After you've settled on your trip dates and duration, book the right Willow Springs holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.