Rosewood Beach Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.

The Whitehall Hotel, BW Premier Collection

Downtown Chicago

$1,099

per person

Sep 17 - Sep 21

found 8 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

Great hotel in an awesome location!

Reviewed on Aug 10, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$1,613

per person

Sep 17 - Sep 21

found 8 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

$1,409

per person

Sep 17 - Sep 21

found 8 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$1,909

per person

Sep 17 - Sep 21

found 8 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

Eurostars Magnificent Mile

Downtown Chicago

$1,323

per person

Sep 17 - Sep 21

found 8 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

Hotel was great and most of the staff was helpful, I did however have to wait an hour for my check luggage and missed my train.

Reviewed on Aug 10, 2026

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

$1,413

per person

Sep 17 - Sep 21

found 8 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

$1,257

per person

Sep 17 - Sep 21

found 8 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

At 3:50 PM, after waiting for an hour to check in, the desk clerk said my room wasn't ready yet. What? He asked me if I had this particular room "on hold". I don't even know what that means. I just wanted a room comparable to the room I reserved. Really, really strange interactions with the desk service. Got a room after some kind of gyrations. I have been here three or four times in last several years. Something has gone wrong at this property. Not returning.

Reviewed on Aug 11, 2026

The Peninsula Chicago

Downtown Chicago

$2,389

per person

Sep 17 - Sep 21

found 8 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

The staff and hotel was fantastic

Reviewed on Aug 10, 2026

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Best Lodging Options Near Rosewood Beach

Renaissance Chicago North Shore Hotel

933 Skokie Blvd Northbrook IL

3.93 km from Rosewood Beach

Book a stay at this golf hotel in Northbrook. Enjoy free parking, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

Courtyard by Marriott Chicago Highland Park/Northbrook

1505 Lake Cook Road Highland Park IL

3.04 km from Rosewood Beach

Book a stay at this business-friendly hotel in Highland Park. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...

Hyatt Regency Deerfield

1750 Lake Cook Rd Deerfield IL

8.38 km from Rosewood Beach

Book a stay at this business-friendly hotel in Deerfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...

Super 8 by Wyndham Deerfield/Northbrook

340 South Waukegan Road Deerfield IL

5.78 km from Rosewood Beach

Book a stay at this business-friendly hotel in Deerfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

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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.