Chicago Water Tower Vacation Deals: Chicago Water Tower, Downtown Chicago Holidays

Chicago Water Tower vacation package deals

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

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $687

per person

Jan 31 - Feb 6

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $707

per person

Jan 31 - Feb 6

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

The Peninsula Chicago

Downtown Chicago

CA $1,902

per person

Jan 31 - Feb 6

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Downtown Chicago

CA $841

per person

Jan 31 - Feb 6

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pendry Chicago

Downtown Chicago

CA $808

per person

Jan 31 - Feb 6

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $988

per person

Feb 23 - Feb 27

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Frequently asked questions

How much are vacation packages to Chicago Water Tower?

Let Travelocity take the worry out of arranging your trip to Chicago Water Tower. Take a look at our excellent CA $687 package deal and save both money and time. With your hotel and flights sorted, you can focus on the fun parts of your getaway — like ticking off those well-known attractions!

Where can I get the best vacation package deals for Chicago Water Tower?

Travelocity has all you need to score an amazing Chicago Water Tower package deal. Select from 400 airlines and 665,000 properties all over the globe and create a travel itinerary that's perfect for you. With so much choice, you'll have plenty of inspiration for your next big getaway.

Why should I purchase my Chicago Water Tower vacation bundle with Travelocity?

Whether you're planning a weeks-long vacation or a last-minute weekend trip, we have many amazing destinations to choose from at an affordable price. What's more, we offer 24/7 customer support, top-notch service and a Price Match Guarantee. Save yourself time and money and lock in your dream vacation now.

Can I go on vacation to Chicago Water Tower at this time?

Our team has all the local knowledge to help make your getaway dreams a reality, so before arranging your trip to Chicago Water Tower, look over our Covid-19 Travel Advisor. Here you'll discover the latest info about quarantine policies, travel restrictions and other useful advice.

Top Chicago Water Tower hotel deals

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $112

CA $131 total

Jan 7 - Jan 8, 2026

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pet-friendly

Free WiFi

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $132

CA $155 total

Jan 7 - Jan 8, 2026

includes taxes & fees

Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pool

Breakfast included

The Whitehall Hotel, BW Premier Collection

105 E Delaware Pl Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $105

CA $124 total

Dec 17 - Dec 18

includes taxes & fees

Book a stay at this boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Breakfast included

Pet-friendly

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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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