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.

The Royal Sonesta Chicago River North

Downtown Chicago

Save 100% on your flight

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Chicago River Side Suites

Downtown Chicago

Save 100% on your flight

per person

Jul 25 - Jul 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, daily housekeeping, and slippers. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) 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.

Kimpton Gray Hotel by IHG

Downtown Chicago

Save 100% on your flight

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.

theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

Stay at this 4.5-star 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.

Virgin Hotels Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park 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 $688 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

CA $268

CA $315 total

includes taxes & fees

Jun 9 - Jun 10

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 Art Institute of Chicago are located nearby.

Free WiFi

Restaurant

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $216

CA $254 total

includes taxes & fees

Jun 29 - Jun 30

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

River Hotel

75 East Wacker Drive, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $275

CA $323 total

includes taxes & fees

Jun 3 - Jun 4

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

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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.