Does Woodlawn have any 4-star all-inclusive resorts?

Finding your dream resort in Woodlawn is as simple as entering your travel dates and destination, and clicking on our "All inclusive" filter. Stay and play where almost everything is already taken care of like your meals, room, entertainment and activities, or go for a standard 4-star resort in or around this sought-after destination.

The Best 4 Star Hotels in Woodlawn, IL from AED 629

613-28 Japanese Island Jackson Park Chicago

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Check availability on Woodlawn 4 Star Hotels

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Our top choices for Woodlawn 4-star hotels

Hyatt Regency O'Hare Chicago

Rosemont

Ifedayo

AED 666 total

includes taxes & fees

28 Jun - 29 Jun

Fairmont Chicago at Millennium Park

Downtown Chicago

MIRCEA

AED 976 total

includes taxes & fees

7 Jul - 8 Jul

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Sabrina

AED 980 total

includes taxes & fees

1 Jul - 2 Jul

Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Krysta

AED 920 total

includes taxes & fees

6 Jul - 7 Jul

The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Zhiwen

AED 683 total

includes taxes & fees

6 Jul - 7 Jul

55-inch LCD TV with cable channels, TV, pay movies

L7 Chicago by LOTTE

Downtown Chicago

Peggy

AED 1,305 total

includes taxes & fees

1 Jul - 2 Jul

Hotel Riu Plaza Chicago

Downtown Chicago

Corey

AED 803 total

includes taxes & fees

30 Jun - 1 Jul

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Dylan

AED 691 total

includes taxes & fees

30 Jun - 1 Jul

The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Brian

AED 697 total

includes taxes & fees

1 Jul - 2 Jul

Hilton Chicago

Downtown Chicago

Ruben

AED 964 total

includes taxes & fees

2 Jul - 3 Jul

Eurostars Magnificent Mile

Downtown Chicago

Audrey

AED 699 total

includes taxes & fees

1 Jul - 2 Jul

Hyatt Regency Chicago

Downtown Chicago

Marianne

AED 973 total

includes taxes & fees

2 Jul - 3 Jul

The Royal Sonesta Chicago Downtown

Downtown Chicago

Sunil

AED 812 total

includes taxes & fees

2 Jul - 3 Jul

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Erin

AED 934 total

includes taxes & fees

9 Jul - 10 Jul

Freehand Chicago

Downtown Chicago

John

AED 629 total

includes taxes & fees

7 Jul - 8 Jul

Arlo Chicago

Downtown Chicago

Tammy

AED 821 total

includes taxes & fees

6 Jul - 7 Jul

The Wade

Downtown Chicago

Molly

AED 852 total

includes taxes & fees

1 Jul - 2 Jul

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Alondra

AED 738 total

includes taxes & fees

2 Jul - 3 Jul

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Mirna

AED 1,001 total

includes taxes & fees

2 Jul - 3 Jul

Sofitel Chicago Magnificent Mile

Downtown Chicago

Ellie

AED 1,127 total

includes taxes & fees

5 Jul - 6 Jul

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Explore similar 5-star hotels

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

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

AED 1,722

AED 2,047 total

28 Jun - 29 Jun

includes taxes & fees

9.6/10 Exceptional! (1,888 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.

Top Woodlawn Hotel Reviews

Hyatt Regency McCormick Place Chicago

10/10 Excellent

"Very convenience when you are working or visiting the convention center!"

Hotel Riu Plaza Chicago

6/10 Okay

"The room was relatively small. The front desk agent who helped with check-in was not friendly at all and gave minimal explanation (she only said the breakfast hours but didn't bother to mention which floor the restaurant is on). The wifi never worked. The rooftop bar was closed without explanation on June 8th, 2026. When I arrived, there was only a signage board and no employees. Thus, the lobby bar was crowded, and the cleaning wasn't thorough. The location is good, but the room size is like the regular hotels in Japan (considered small in the USA). If it is a business hotel with no working Wi-Fi, I won't be staying here, even if the price is reasonable for the location. For family/leisure purposes, the room is too small, and the mediocre service wouldn't help create a memorable stay experience either."

The Chicago Hotel Collection - Magnificent Mile

6/10 Okay

"It was unfortunate that for entire day I did not have air-conditioning in my room. The staff indicated that there was a problem with the entire hotel and the HVAC system, and that the engineer was working on it. However, the next day I found out when the engineer came to my room that whatever motor that they used to install an air conditioning unit in the room was the incorrect motor and it was never gonna work. The air conditioning unit was finally fixed and when I came back to the hotel the next day by 3 PM we had air-conditioning. The hotel indicated that they were going to reimburse us for the first night. Stay to the amount of $389 and that they would be contacting Expedia since that is where I booked the original trip through. Therefore, I’m just waiting for a refund for my first night which the hotel told me was $389."

Frequently asked questions

What are the best 4-star hotels in Woodlawn?

When you plan your accommodations at Sophy Hyde Park, you can count on exceptional service, comfortable rooms and plenty of amenities. This 4-star hotel located conveniently around Woodlawn consistently receives top marks from our guests.

How much does it cost to stay in a 4-star hotel in Woodlawn?

To book a 4-star hotel in Woodlawn that's within your budget, use Expedia's search and sort filters. Check out the available options during your getaway dates and use our pricing filter to set your limit. You can also sort your results by the cheapest option first.

Search for the lowest price from AED 2,047

What's the difference between 5-star and 4-star hotels in Woodlawn?

If you decide to vacation at a 4-star hotel in Woodlawn, you'll usually find plenty of amenities to make sure you're relaxed, such as a gym, pool and restaurant. You can look forward to excellent service and upscale surroundings. Go for a 5-star hotel and you'll have access to a few more perks — think concierge assistance, on-site spas and indulgent turndown services. You're likely to get more amenities and first-rate services at a 5-star stay, though both are awesome options for luxury guests.

Find 4 Star Hotels in Woodlawn, IL from AED 629

Change your mind

Treat yourself

Be picky

Check availability on Woodlawn 4 Star Hotels

Our top choices for Woodlawn 4-star hotels

Hyatt Regency O'Hare Chicago

Fairmont Chicago at Millennium Park

InterContinental Chicago Magnificent Mile by IHG

Embassy Suites by Hilton Chicago Downtown River North

The Chicago Hotel Collection Ambassador Gold Coast

L7 Chicago by LOTTE

Hotel Riu Plaza Chicago

Hotel Felix River North/Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

Hilton Chicago

Eurostars Magnificent Mile

Hyatt Regency Chicago

The Royal Sonesta Chicago Downtown

The Allegro Royal Sonesta Hotel Chicago Loop

Freehand Chicago

Arlo Chicago

The Wade

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Sheraton Grand Chicago Riverwalk

Sofitel Chicago Magnificent Mile

Explore similar 5-star hotels

Trump International Hotel & Tower Chicago

Top Woodlawn Hotel Reviews

Hyatt Regency McCormick Place Chicago

Frequently asked questions

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Woodlawn Hotels by Star Rating

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