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.

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,339

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) 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.

Level Chicago Fulton Market

Downtown Chicago

CA $1,770

per person

Nov 10 - Nov 15

found 7 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,500

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) 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.

Swissotel - Chicago

Downtown Chicago

CA $1,492

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

CA $1,374

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 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 Michigan Avenue and Chicago Riverwalk are located nearby.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,581

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. 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 Oak Street Beach?

If you'd like to enjoy stress-free planning and impressive savings, our CA $1,339 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 $197

CA $234 total

Aug 31 - Sep 1

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

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Kitchen

Washer

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $744

CA $885 total

Aug 30 - Aug 31

includes taxes & fees

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 in our reviews. Popular attractions Michigan Avenue 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.

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