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.

Hilton Garden Inn Naperville/Warrenville

per person

Jul 4 - Jul 9

found 8 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 3-star business-friendly hotel in Warrenville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Nike Sports Complex and Odyssey Fun World are located nearby.

Chicago River Side Suites

Downtown Chicago

Save 100% on your flight

per person

Aug 5 - Aug 9

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, daily housekeeping, and slippers. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

per person

Jul 4 - Jul 9

found 8 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) 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.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

per person

Jul 4 - Jul 9

found 8 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) 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 Michigan Avenue and Chicago Riverwalk are located nearby.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Jul 15 - Jul 22

found 20 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

Stay at this 3.5-star 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.

The Peninsula Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 5 - Aug 9

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition 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 $695 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

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $253

CA $297 total

includes taxes & fees

Jun 29 - Jun 30

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

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $253

CA $339 total

includes taxes & fees

Jun 29 - Jun 30

Stay at this 4.5-star 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.

Spa

Pet-friendly

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $77

CA $270 total

includes taxes & fees

Jun 3 - Jun 4

Stay at this 4-star 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

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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.