Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 321,000 hotels worldwide.

Get the best price available for your trip.

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Featured Oak Street Beach Luxury Hotels

See all 569 Hotels in Oak Street Beach
W Chicago - Lakeshore

W Chicago - Lakeshore

644 N Lake Shore Dr, Chicago
4.5 out of 5.0
4.0 out of 5 (2,359 reviews)
It was so great Clean amazing veiw staff is so nice
  Nov 23, 2017

$127

$127
Map

Recently booked Luxury Hotels in Oak Street Beach

W Chicago - Lakeshore
4.5 out of 5.0
Last booking: 31 hours ago

A weekend away keeps your stress at bay, especially when you're enjoying a stay in Oak Street Beach. Delicious eats, tremendous activities, and the most coveted photo opportunities: these are just some of the benefits of visiting Oak Street Beach. Naturally, you'll stay at a luxury hotel! Sampling the finer things in life is just your speed. While you're here, you'll also snag seats to the most sought-after shows, treat yourself to the city's best food, and get in line to see the coolest attractions. Book your luxury hotel in Oak Street Beach on Expedia.com right now and start your trip off on the right (well-dressed) foot.

5-Star Vacations in Oak Street Beach

It turns out plenty of folks love Oak Street Beach enough to have set down roots -- how is that for proof that Oak Street Beach is teeming with an intoxicating assortment of activities? No matter what brings you to Oak Street Beach, the destination always delivers. Oak Street Beach is full of comfy hotels as well as fantastic food, so you can count on a fantastic stay. Book early to get a room with a view!

Any 5-star getaway calls for pedicures, culture, and activities from your bucket list. When you book your travel on Expedia.com, it's all at your fingertips. Thanks to our incredible prices on hotels, you'll still have plenty of cash for the most popular things to do. After many hours of exploration, your luxury hotel is waiting with a wonderful meal and upscale amenities. Don't fall asleep before soaking in your over-sized tub or asking the concierge for advice on tomorrow's plans. The luxury rooms and suites in Oak Street Beach will have you basking in tranquility in no time.

Find Luxury Oak Street Beach Hotels Now

When you’ve got your heart set on an upscale escape in Oak Street Beach, Expedia.com is here to make the process painless. Browse the bounty of reviews on spectacular hotels to find an accommodation that suits your needs. 5-Star hotels treat you right, offering things like high end bath amenities and private hot tubs. Some of the city's deluxe accommodations even feature upscale penthouses, while others have tennis courts or salt water pools. Use our easy booking widget to choose an incredible 5-star hotel in Oak Street Beach, and before you know it you'll be feeling blissful in paradise!