Marriott Marquis Chicago 
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8.5 (314 Reviews) Hotel
Breakfast • Private parking • 4 restaurants
Chicago Near South Side • In Oakland · 3.6km to center
Best Price Match Oakland Luxury Rental Homes and Villas
Find Luxury Places to Stay Near Oakland. Find luxury in Oakland, Chicago.
The Study at the University of Chicago Best Price Match
9.1 (1047 Reviews) Hotel
Private parking • Restaurant • Pet friendly
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Sophy Hyde Park Best Price Match
9.0 (202 Reviews) Hotel
Private parking • Restaurant • Pet friendly
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Hyatt Regency McCormick Place Chicago Best Price Match
8.2 (827 Reviews) Hotel
Breakfast • Private parking • 3 restaurants
Chicago Near South Side • In Oakland · 3.4km to center
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Hamaline Luxury Guest House Best Price Match
8.5 (7 Reviews) Villa
The entire place is yours • 1400 m² size • Free on-site parking
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Chic Euro City Getaway- Close to Downtown Best Price Match
8.4 (29 Reviews) Apartment
The entire place is yours • 111 m² size • Free WiFi
Chicago Grand Boulevard • In Oakland · 2.5km to center
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Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena Best Price Match
8.9 (194 Reviews) Apartment
The entire place is yours • 60 m² size • Kitchen
Chicago Near South Side • In Oakland · 3.8km to center
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The Penthouse, Lux stay near Downtown, UofC & Lake Best Price Match
9.2 (37 Reviews) Apartment
The entire place is yours • 135 m² size • Kitchen
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Stylish Urban Retreat 3 Bedroom Newly Remodeled Best Price Match
8.3 (32 Reviews) Apartment
The entire place is yours • 111 m² size • Free on-site parking
Chicago Grand Boulevard • In Oakland · 1.5km to center
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Chicago 2BR Suite Perfect for Convention and Business Trips Near McCormick Place, Arena, Soldier Field and Grant Park Best Price Match
8.6 (31 Reviews) Apartment
The entire place is yours • 88 m² size • Kitchen
Chicago Near South Side • In Oakland · 3.9km to center
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Modern 2BR in South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail Best Price Match
8.0 (35 Reviews) Apartment
The entire place is yours • 88 m² size • Private parking
Chicago Near South Side • In Oakland · 3.8km to center
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Forrestville Ave Large Suite Best Price Match
8.6 (103 Reviews) Apartment
The entire place is yours • 130 m² size • Free parking
Chicago Grand Boulevard • In Oakland · 1.5km to center
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McCormick Place 3BR Luxury Penthouse Duplex with Personal Rooftop and Optional Parking for 8 guests in Chicago South Loop Best Price Match
9.7 (7 Reviews) Apartment
The entire place is yours • 220 m² size • Private parking
Chicago Near South Side • In Oakland · 3.9km to center
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Beautifully Renovated House 10 mins from Downtown Best Price Match
8.3 (12 Reviews) Holiday_home
The entire place is yours • 297 m² size • Kitchen
Chicago Grand Boulevard • In Oakland · 1.6km to center
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Eco Stay by UChicago, Lakefront & Hyde Park! Best Price Match
9.0 (5 Reviews) Apartment
The entire place is yours • 74 m² size • Free on-site parking
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The Brown House - A luxurious UChicago Campus stay Best Price Match
10.0 (5 Reviews) Apartment
The entire place is yours • 139 m² size • Free on-site parking
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Modern 3BR in South Loop with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field Best Price Match
9.4 (12 Reviews) Apartment
The entire place is yours • 102 m² size • Private parking
Chicago Near South Side • In Oakland · 3.9km to center
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Location! Location! 2bd 1bth spacious apartment! Best Price Match
8.3 (13 Reviews) Apartment
The entire place is yours • 48 m² size • Free on-site parking
Chicago Bridgeport • In Oakland · 4.0km to center
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Bridgeport Place - free parking, McCormick Place-Sox Park Best Price Match
9.1 (17 Reviews) Apartment
The entire place is yours • 60 m² size • Free parking
Chicago Bridgeport • In Oakland · 4.7km to center
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Spacious Bronzeville Apartment Best Price Match
9.8 (5 Reviews) Apartment
The entire place is yours • 139 m² size • Free WiFi
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Cozy & Radiant 2BR Apartment - BStone 605 Best Price Match
8.5 (6 Reviews) Apartment
The entire place is yours • 124 m² size • Pet friendly
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McCormick Place Huge 2BR Cozy Loft Suite with Optional Parking Sleeps 8 Near Soldier Field and Grant Park Best Price Match
9.1 (9 Reviews) Apartment
The entire place is yours • 102 m² size • Private parking
Chicago Near South Side • In Oakland · 3.9km to center
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South Loop 2BR Getaway with Smart TVs & Optional Parking Near McCormick Place, Museum Campus & Downtown Best Price Match
8.2 (17 Reviews) Apartment
The entire place is yours • 79 m² size • Kitchen
Chicago Near South Side • In Oakland · 3.9km to center
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Spacious 2BR Vacation Rental with City View, Optional Parking and Gym Near McCormick Place & Downtown Chicago Attractions Best Price Match
8.2 (16 Reviews) Apartment
The entire place is yours • 88 m² size • Private parking
Chicago Near South Side • In Oakland · 3.9km to center
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Sleek 1-Bedroom Apt in Chicago - East Park Tower 0610 rep Best Price Match
8.8 (6 Reviews) Apartment
The entire place is yours • 58 m² size • Pet friendly
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Convenient 2BR Suite in Prime Location with Gym Access & Optional Parking Near McCormick Place and Soldier Field Best Price Match
8.8 (9 Reviews) Apartment
The entire place is yours • 80 m² size • Private parking
Chicago Near South Side • In Oakland · 3.9km to center
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Bright 2BR Apt with Gym and Optional Parking Near Soldier Field, Museum Campus, McCormick Place Best Price Match
8.4 (5 Reviews) Apartment
The entire place is yours • 88 m² size • Private parking
Chicago Near South Side • In Oakland · 3.8km to center
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South Loop 3 Bedroom Apt Best Price Match
8.5 (7 Reviews) Apartment
The entire place is yours • 111 m² size • Free WiFi
Chicago Near South Side • In Oakland · 5.0km to center
Best Price Match About Oakland Luxury Rental on NearbyHoliday
Looking for luxury in Oakland? Compare top options in Chicago.
Searching for a luxury place to stay in or near Oakland? We have more than 28 luxury homes, private retreats, luxury villas, 5-star hotels, cottages, and condos that you can stay at in Oakland.
NearbyHoliday has a variety of luxury rentals, including vacation homes, apartments, chalets, luxury penthouses, lake homes, beachfront resorts, private villas, and many luxury lifestyle options, many in Oakland. Whether you are traveling with families or groups, hosting a get-together, or a cocktail party, we have the perfect place to stay for your travel plans. Our places to stay in Oakland are located in the top buildings and neighborhoods and many come with luxury features throughout the living areas, kitchens, and bedrooms, including private pools, hot tubs, home theatres, amazing views, and plenty of space to relax. Get more room with NearbyHoliday.