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.

The Emily Hotel

Downtown Chicago

CA $614

per person

Nov 23 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Chicago (ORD)

Stay at this 4-star 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.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $631

per person

Nov 23 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,373

per person

Oct 30 - Nov 2

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 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.

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

CA $1,009

per person

Oct 25 - Oct 28

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

Stay at this 4.5-star 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.

The Peninsula Chicago

Downtown Chicago

CA $1,703

per person

Nov 21 - Nov 25

found 23 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) 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.

Hilton Chicago O'Hare Airport

O'Hare

CA $684

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Chicago (ORD)

Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex 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 $614 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

Free cancellation

Reserve now, pay when you stay

CA $254

CA $298 total

Sep 22 - Sep 23

includes taxes & fees

Stay at this 4-star 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 $221

CA $260 total

Sep 22 - Sep 23

includes taxes & fees

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 Wade

644 N Lake Shore Dr, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $230

CA $270 total

Sep 22 - Sep 23

includes taxes & fees

Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.

Pool

Pet-friendly

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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.