5 Stars Hotels in Woodlawn: Compare Hotel Prices & Find the Cheapest Woodlawn, Chicago 5 Stars Hotels

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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

NT$19,110 total

includes taxes & fees

Dec 6 - Dec 7

A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Matthew

NT$17,989 total

includes taxes & fees

Nov 15 - Nov 16

A rooftop bar with seating and a view of the city skyline at night.

3. The Peninsula Chicago

Downtown Chicago

Vincent Haley

NT$23,400 total

includes taxes & fees

Dec 6 - Dec 7

A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

4. The Langham, Chicago

Downtown Chicago

Courtney

NT$20,358 total

includes taxes & fees

Dec 6 - Dec 7

A hotel entrance with a fountain, a car, and a person standing by the entrance.

5. Waldorf Astoria Chicago

Downtown Chicago

Luis

NT$17,404 total

includes taxes & fees

Dec 6 - Dec 7

A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.

6. The Ritz-Carlton, Chicago

Downtown Chicago

Krikour

NT$15,357 total

includes taxes & fees

Dec 6 - Dec 7

A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.

7. Nobu Hotel Chicago

Downtown Chicago

Abhay

NT$14,391 total

includes taxes & fees

Nov 22 - Nov 23

A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.

8. Park Hyatt Chicago

Downtown Chicago

Marissa

NT$17,073 total

includes taxes & fees

Nov 25 - Nov 26

A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.

9. The St. Regis Chicago

Downtown Chicago

Alise

NT$20,922 total

includes taxes & fees

Nov 22 - Nov 23

A rooftop dining area with checkered tablecloths, red and blue plates, and a city skyline in the background.

10. Art Villa

West Town

Top Woodlawn Hotel Reviews

Nobu Hotel Chicago

Downtown Chicago

10/10 Excellent

William

Trump International Hotel & Tower Chicago

Downtown Chicago

10/10 Excellent

Tammy Lynn

The Peninsula Chicago

Downtown Chicago

10/10 Excellent

Excellent hotel, my only complaint would be the Peninsula food service. We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely wasn’t. The whole Peking duck was arranged haphazardly on the plate, the skin was not really crispy, and the taste experience was completely lackluster. As to the main dining room the service...

Michael

Park Hyatt Chicago

Downtown Chicago

10/10 Excellent

KEVIN

Four Seasons Hotel Chicago

Downtown Chicago

10/10 Excellent

Pamela

Frequently Asked Questions

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

The amount you pay for a 5-star hotel in Woodlawn depends on things such as when you want to go and the length of your break. An insider tip for bagging the best deal? Use our pricing filters to check out the available accommodations for your chosen dates.

Search for the lowest price per night from NT$11,414

What makes a hotel 5 stars in Woodlawn?

In Woodlawn, a hotel needs to offer a certain level of upscale features to earn 5 stars. These may include on-site gyms, gourmet restaurants, saunas and spas, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their guest-focused service. You'll enjoy things like concierge services, in-room massages and nightly turn-down services. Some may also offer special touches such as welcome gifts.

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

Use our filters to find a high-end retreat in Woodlawn where everything you need is included. Next, refine your results for accommodations that have 5 stars and are deemed "All inclusive." The main thing on the agenda at these stays? Pure enjoyment and indulgence.

Are there any 5-star vacation rentals in Woodlawn?

There are no 5-star vacation rentals in Woodlawn on our site, but there are some other highly rated properties worth looking into. Browse our vacation rentals in Woodlawn to discover the ideal place for your stay.

Woodlawn 5 Stars Hotels

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Woodlawn 5-star hotels

1. Four Seasons Hotel Chicago

2. Trump International Hotel & Tower Chicago

3. The Peninsula Chicago

4. The Langham, Chicago

5. Waldorf Astoria Chicago

6. The Ritz-Carlton, Chicago

7. Nobu Hotel Chicago

8. Park Hyatt Chicago

9. The St. Regis Chicago

10. Art Villa

Top Woodlawn Hotel Reviews

Nobu Hotel Chicago

10/10 Excellent

Frequently Asked Questions

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

What makes a hotel 5 stars in Woodlawn?

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

Are there any 5-star vacation rentals in Woodlawn?

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