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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,233

per person

Nov 11 - Nov 15

found 22 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

CA $1,238

per person

Nov 12 - Nov 18

found 18 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,430

per person

Nov 11 - Nov 15

found 22 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,727

per person

Nov 11 - Nov 14

found 14 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) 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.

The Emily Hotel

Downtown Chicago

CA $1,456

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. 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 United Center and Chicago Riverwalk are located nearby.

Pendry Chicago

Downtown Chicago

CA $1,537

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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.

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 $1,233 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

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $204

CA $242 total

Nov 1 - Nov 2

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). 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

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $195

CA $232 total

Nov 1 - Nov 2

includes taxes & fees

Book a stay at this boutique 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 Michigan Avenue and Chicago Riverwalk are located nearby.

Pet-friendly

Free WiFi

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $165

CA $197 total

Nov 2 - Nov 3

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). 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

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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.

Things to do in Chicago