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.

Level Chicago – Old Town

Downtown Chicago

CA $748

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

Stay at this 4-star 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,232

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Calgary (YYC) 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.

The Royal Sonesta Chicago River North

Downtown Chicago

CA $875

per person

Oct 19 - Oct 23

found 15 hours ago

Roundtrip non-stop flight included

Saskatoon (YXE) 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.

Pendry Chicago

Downtown Chicago

CA $865

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Calgary (YYC) 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.

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

CA $962

per person

Oct 19 - Oct 23

found 15 hours ago

Roundtrip non-stop flight included

Saskatoon (YXE) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

The Langham, Chicago

Downtown Chicago

CA $1,315

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Calgary (YYC) 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.

Frequently asked questions

How much are vacation packages to Chicago Riverwalk?

Bag an express ticket to an amazing deal with Travelocity's CA $748 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

The Wade

644 N Lake Shore Dr, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $208

CA $245 total

Sep 1 - Sep 2

includes taxes & fees

Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.

Pool

Pet-friendly

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

CA $222

CA $260 total

Sep 3 - Sep 4

includes taxes & fees

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

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $239

CA $315 total

Sep 2 - Sep 3

includes taxes & fees

Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Pool

Spa

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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.