Oak Street Beach Vacation Deals: Oak Street Beach, Downtown Chicago Holidays

Oak Street Beach vacation package deals

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

theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $508

per person

Feb 15 - Feb 21

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) 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 Westin Michigan Avenue Chicago

Downtown Chicago

CA $964

per person

Dec 25 - Dec 31

found 2 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

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

Pendry Chicago

Downtown Chicago

CA $657

per person

Feb 15 - Feb 21

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) 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 $1,322

per person

Feb 15 - Feb 21

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) 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.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $632

per person

Feb 15 - Feb 21

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) 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.

Arlo Chicago

Downtown Chicago

CA $732

per person

Feb 15 - Feb 21

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Frequently asked questions

How much are vacation packages to Oak Street Beach?

If you'd like to enjoy stress-free planning and impressive savings, our CA $508 Oak Street Beach vacation package will be just the ticket. With your flights and hotels sorted, organizing your getaway around this amazing attraction has never been more simple.

Where can I get the best vacation package deals for Oak Street Beach?

No matter your travel style, Travelocity can help you snap up an unbeatable Oak Street Beach package deal. All you need to do is pick and choose between our 400 airlines and 665,000 properties worldwide.

Why should I purchase my Oak Street Beach vacation bundle via Travelocity?

You'll not only save loads, but you can also access our round-the-clock support, top-notch service and a Price Match Guarantee. Roam across the globe, discover hidden treasures and create lifelong memories — we'll take care of the important details.

Can I go on vacation to Oak Street Beach at this time?

Our team has all the local knowledge to ensure your vacation dreams a reality, so before planning your trip to Oak Street Beach, read through our Covid-19 Travel Advisor. Here you'll discover the latest info about travel restrictions, quarantine policies and other important details.

Top Oak Street Beach 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 $123

CA $144 total

Dec 21 - Dec 22

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

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $118

CA $138 total

Dec 7 - Dec 8

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

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $146

CA $206 total

Dec 21 - Dec 22

includes taxes & fees

Book a stay at this luxury 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

Don't see what you're looking for?

See all available properties in Oak Street Beach

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