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 $622

per person

Jan 18 - Jan 24

found 1 day ago

Roundtrip flight included

Toronto (YYZ) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $835

per person

Jan 23 - Jan 26

found 1 day 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.

Viceroy Chicago

Downtown Chicago

CA $1,529

per person

Dec 28 - Jan 4

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

CA $749

per person

Feb 15 - Feb 21

found 10 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Sentral Michigan Avenue

Downtown Chicago

CA $1,037

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.

Victoria Resort and Bed & Breakfast

North Side

CA $1,297

per person

Feb 14 - Feb 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Michigan Maritime Museum and Warner Vineyards 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 $622 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

CA $123

per night

Dec 21 - Dec 22

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

per night

Dec 7 - Dec 8

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 $156

per night

Dec 21 - Dec 22

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

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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