Chicago Riverwalk Vacation Deals: Chicago Riverwalk, Downtown Chicago Holidays

Chicago Riverwalk vacation package deals

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

Pendry Chicago

Downtown Chicago

CA $452

per person

Nov 26 - Nov 28

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,706

per person

Dec 23 - Dec 28

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this 5-star 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.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $468

per person

Nov 26 - Nov 28

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

Stay at this 3.5-star 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.

Park Hyatt Chicago

Downtown Chicago

CA $1,051

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago - River North

Downtown Chicago

CA $547

per person

Dec 12 - Dec 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Grand Royal Hotel O'Hare - Chicago

CA $624

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Woodfield Mall are located nearby.

Frequently asked questions

How much are vacation packages to Chicago Riverwalk?

Bag an express ticket to an amazing deal with Travelocity's CA $452 Chicago Riverwalk vacation package. Not only can you save a tidy sum on your return flights and hotel, you can also add on a few fun local experiences or even a rental vehicle.

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

You can grab amazing Chicago Riverwalk package deals with Travelocity. Mix and match from as many as 400 airlines and 665,000 worldwide properties and turn those travel dreams into reality.

Why should I book my Chicago Riverwalk vacation bundle via Travelocity?

From exciting destinations to one-of-a-kind experiences, we have everything you need to appease your wanderlust. Our 24/7 support will also make sure you're taken care of while you're on your trip. And don't worry if you find a cheaper price on your reservation, we'll match it. That's our Price Match Guarantee.

Can I go on vacation to Chicago Riverwalk at this time?

We have the local know-how to ensure your travel dreams come true, so before arranging your trip to Chicago Riverwalk, check out our Covid-19 Travel Advisor. Here you'll find all the latest info about travel restrictions, quarantine policies and a whole lot more.

Top Chicago Riverwalk hotel deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Free WiFi

Restaurant

Freehand Chicago

19 East Ohio Street, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $107

CA $151 total

Nov 10 - Nov 11

includes taxes & fees

Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pet-friendly

Free WiFi

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $184

CA $216 total

Nov 9 - Nov 10

includes taxes & fees

Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Free WiFi

Restaurant

Don't see what you're looking for?

See all available properties in Chicago Riverwalk

View all properties

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.

Things to do in Chicago