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

Woodlawn 5 Stars Hotels

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Check availability on Woodlawn 5 Star Hotels

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

Our top choices for Woodlawn 5-star hotels

Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,002 reviews)
"Liked the layout of our suite and that the hotel was right inside the shopping Mall & Bloomingdales."
United States
August
The price is NT$17,122
NT$20,357 total
includes taxes & fees
Aug 9 - Aug 10
Four Seasons Hotel Chicago
Terrace/patio

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,958 reviews)
"Great location and wonderful staff."
United States
Ryan
The price is NT$15,143
NT$18,004 total
includes taxes & fees
Aug 16 - Aug 17
Trump International Hotel & Tower Chicago
Lobby

3. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,000 reviews)
"Wonderful hotel stay"
United States
Robert
The price is NT$17,566
NT$20,885 total
includes taxes & fees
Aug 30 - Aug 31
The Langham, Chicago
Exterior

4. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,001 reviews)
"Beautiful property and excellent service from all staff."
United States
Jim
The price is NT$17,300
NT$20,568 total
includes taxes & fees
Aug 23 - Aug 24
Waldorf Astoria Chicago
Front of property - evening/night

5. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,000 reviews)
"Welcoming and attentive staff throughout the hotel made my stay an enjoyable and memorable experience."
United States
Charles
The price is NT$20,191
NT$24,005 total
includes taxes & fees
Aug 9 - Aug 10
The Peninsula Chicago
Cafe

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
"I have stayed at this hotel a few times and each time it is better than the last. Great service, great location. Can’t wait to come back again."
United States
Caryn
The price is NT$15,378
NT$18,283 total
includes taxes & fees
Aug 23 - Aug 24
The Ritz-Carlton, Chicago
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers

7. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (895 reviews)
"The breakfast is a must try there."
United States
Yidong
The price is NT$14,297
NT$17,806 total
includes taxes & fees
Aug 23 - Aug 24
Nobu Hotel Chicago
Breakfast, lunch, dinner and brunch served

8. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,000 reviews)
"Our room was wonderful"
United States
Jennifer
The price is NT$17,881
NT$21,259 total
includes taxes & fees
Aug 9 - Aug 10
Park Hyatt Chicago
2 restaurants; breakfast, lunch, dinner, and brunch served

9. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (128 reviews)
"We had a great stay and will come back again in the near future!"
United States
Princess
The price is NT$18,188
NT$21,624 total
includes taxes & fees
Aug 23 - Aug 24
The St. Regis Chicago
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio

10. Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2 reviews)
Art Villa
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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.
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL
The price is NT$5,460 per night from Aug 30 to Aug 31
NT$5,460
NT$6,223 total
Aug 30 - Aug 31
includes taxes & fees
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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$5,837

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.

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