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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

per person

Mar. 11 - Mar. 14

found 4 hours ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Fairmont Chicago at Millennium Park

Downtown Chicago

per person

Apr. 16 - Apr. 21

found 7 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

Book a stay at this spa 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 Millennium Park and Chicago Riverwalk are located nearby.

Level Chicago - River North

Downtown Chicago

per person

Mar. 2 - Mar. 7

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Theatre and Michigan Avenue are located nearby.

Pendry Chicago

Downtown Chicago

per person

Mar. 6 - Mar. 9

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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 Millennium Park and Michigan Avenue are located nearby.

Viceroy Chicago

Downtown Chicago

per person

Apr. 16 - Apr. 21

found 7 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Aloft Chicago Mag Mile

Downtown Chicago

per person

Apr. 16 - Apr. 21

found 7 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the bar in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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 $729 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.