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.

Hilton Orrington / Evanston

per person

Jan. 31 - Feb. 3

found 20 hours ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clark Street Beach and Halim Time & Glass Museum are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

per person

Mar. 2 - Mar. 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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.

Hotel Riu Plaza Chicago

Downtown Chicago

per person

Jan. 28 - Feb. 2

found 11 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Viceroy Chicago

Downtown Chicago

per person

Mar. 2 - Mar. 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Downtown Chicago

per person

Jan. 23 - Jan. 27

found 18 hours ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

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

Aloft Chicago Mag Mile

Downtown Chicago

per person

Mar. 2 - Mar. 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the bar in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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 $538 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

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $145

CA $170 total

includes taxes & fees

12 Jan - 13 Jan 2025

Stay at this 4-star 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

River Hotel

75 East Wacker Drive, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $132

CA $155 total

includes taxes & fees

17 Jan - 18 Jan 2025

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

Pet-friendly

Free WiFi

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $200

CA $276 total

includes taxes & fees

10 Jan - 11 Jan 2025

Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Free WiFi

Restaurant

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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.