Are there any 5-star vacation rentals in Woodlawn?

Although there aren't any 5-star vacation rentals in Woodlawn on our site, we have a range of properties that promise a memorable getaway. Discover one that suits your style by checking out our vacation rentals in Woodlawn .

The Best 5 Star Hotels in Woodlawn, IL from AED 502

A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

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Our top choices for Woodlawn 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.

1. Four Seasons Hotel Chicago

Downtown Chicago

ryan

AED 2,140 total

includes taxes & fees

6 Dec - 7 Dec

A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Matthew

AED 2,014 total

includes taxes & fees

15 Nov - 16 Nov

A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

3. The Peninsula Chicago

Downtown Chicago

Vincent Haley

AED 2,620 total

includes taxes & fees

6 Dec - 7 Dec

A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

4. The Langham, Chicago

Downtown Chicago

Courtney

AED 2,279 total

includes taxes & fees

6 Dec - 7 Dec

A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

5. Waldorf Astoria Chicago

Downtown Chicago

Luis

AED 1,949 total

includes taxes & fees

6 Dec - 7 Dec

A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

6. The Ritz-Carlton, Chicago

Downtown Chicago

Krikour

AED 1,719 total

includes taxes & fees

6 Dec - 7 Dec

A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

7. Nobu Hotel Chicago

Downtown Chicago

Abhay

AED 1,610 total

includes taxes & fees

22 Nov - 23 Nov

A couple dining at a table with a view of a cityscape and a sunset.

8. Park Hyatt Chicago

Downtown Chicago

Marissa

AED 1,912 total

includes taxes & fees

22 Nov - 23 Nov

A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

9. The St. Regis Chicago

Downtown Chicago

Alise

AED 2,341 total

includes taxes & fees

22 Nov - 23 Nov

A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.

10. Art Villa

West Town

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Woodlawn.

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL

AED 437

AED 520 total

3 Dec - 4 Dec

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Woodlawn?

How much you pay for a 5-star hotel in Woodlawn can vary depending on the time of year you travel and how long you plan to be away, among other factors. Take advantage of our price per night filter and other search tools to find the best rate on a luxurious getaway.

Search for the lowest price per night from AED 502

What makes a hotel 5 stars in Woodlawn?

Outstanding guest service is at the heart of every 5-star hotel in Woodlawn. From the instant you arrive, staff are at your beck and call, whether arranging valet parking or providing in-room massage treatments. In addition, hotels must offer upscale conveniences to obtain a 5-star rating. These can include luxury bathrooms, saunas or spas, swimming pools, fine dining kitchens and knowledgeable concierge.

Are there any 5-star all-inclusive resorts in Woodlawn?

Use our handy filters to find a high-end escape in Woodlawn where most of what you need is included in the price. Next, refine your results for accommodations that have 5 stars and are deemed "All inclusive." The most important thing on the schedule at these stays? Relaxation and enjoyment.

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