Cleveland Park

Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was €852, price is now €654 per person
€654
per person
1 Feb - 6 Feb
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Our room was very clean, beautiful view, and extremely friendly staff. I would especially like to thank and acknowledge the outstanding customer service from Beth Ann. Her help and kindness were greatly appreciated.

Reviewed on 25 Nov 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,714, price is now €1,215 per person
€1,215
per person
1 Feb - 6 Feb
found 20 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Everything perfect , comfortable room , nice staff make out stay unforgettable.

Reviewed on 27 Nov 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,534, price is now €1,195 per person
€1,195
per person
29 Dec - 2 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.

Reviewed on 25 Nov 2025

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Zilla Park

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Ridgeland Park

Blue Chip Casino

Why not try your luck with a visit to Blue Chip Casino during your travels in Michigan City? Wander the beautiful beaches and lakeside in the area.

Blue Chip Casino

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Top Hotel Deals

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive Michigan City IN
Blue Chip Casino Hotel and Spa
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Michigan City IN
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly

Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly

Michigan City IN
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly
Cozy house with hot tub, firepit, near restaurants + near beach

Cozy house with hot tub, firepit, near restaurants + near beach

2 out of 5
Michigan City IN
Cozy house with hot tub, firepit, near restaurants + near beach
Holiday House! Fully Renovated House, Minutes to EVERYTHING, Pet Friendly!

Holiday House! Fully Renovated House, Minutes to EVERYTHING, Pet Friendly!

2 out of 5
Michigan City IN
Holiday House! Fully Renovated House, Minutes to EVERYTHING, Pet Friendly!
UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach

UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach

Michigan City IN
UP*W/D*King*Balcony*10 min. to IN.Dunes & Beach
Sleeps 6*W/D*10 min. to IN.Dunes & Beach

Sleeps 6*W/D*10 min. to IN.Dunes & Beach

Michigan City IN
Sleeps 6*W/D*10 min. to IN.Dunes & Beach
Newely Remodeled Studio!

Newely Remodeled Studio!

Michigan City IN
Newely Remodeled Studio!
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Michigan City IN
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
See all 1,057 properties in Cleveland Park
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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