Deals on connecting hotel rooms and suites in Chicago

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Chicago’s architectural gems, world-class restaurants, two waterfront views, and Midwestern hospitality keep visitors coming back for more. This beautiful city, located on the shores of Lake Michigan and newly developed Chicago River, has more than 200 distinct neighborhoods, most easily accessible using the subway and elevated train system called the “L.” Stay in the center of it all downtown in The Loop, an area south of the Chicago River that’s brimming with photo ops like 19th-century Art Deco buildings, The Bean sculpture in Millennium Park, and the Willis Tower—Chicago’s tallest skyscraper. This area is also not far from some of the city’s hottest restaurants, many of which are located on West Randolph Street in the West Loop neighborhood. Take in views of the Loop from the Wit’s Luxury Spa King One Bedroom Suite + Classic Two Queen residential-style connected rooms and don’t miss its hip rooftop bar ROOF. One of the Loop’s most stunning high-rise hotels, the Fairmont Chicago Millennium Park, has connected rooms with incredible views like the Signature View Suite King + Signature King Room. In the Magnificent Mile neighborhood, north of the Chicago River, the recently renovated Conrad Chicago boasts lavish connecting rooms with spa-like bathrooms such as the Royal Suite + Two Queen Beds Superior Room, which sleeps up to eight. Nearby at the Chicago Hilton/Magnificent Mile Suites, the stylish One King Bed One Bedroom Suite and Two Double Beds Alcove Suite combine to sleep up to 10. Suiteness agents can help you choose the right hotel and secure tickets to top attractions.

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Starting at $177

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Hampton Inn Chicago Downtown/Magnificent Mile

Starting at $135

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.

Hampton Inn Chicago North Loyola Station

Starting at $222

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.

Hampton Inn & Suites Chicago Downtown

Starting at $201

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.

Hilton Chicago

Starting at $337

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Hilton Chicago O'Hare Airport

Starting at $339

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Hilton Garden Inn Chicago Downtown/Magnificent Mile

Starting at $241

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Hilton Garden Inn Chicago Downtown South Loop

Starting at $161

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Hilton Garden Inn Chicago McCormick Place

Starting at $233

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Hilton Garden Inn Chicago/Midway Airport

Starting at $204

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Hilton Rosemont/Chicago O'Hare

Starting at $214

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Home2 Suites by Hilton Chicago McCormick Place

Starting at $169

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.

Home2 Suites by Hilton Chicago River North

Starting at $159

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.

Homewood Suites by Hilton Chicago-Downtown

Starting at $178

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Starting at $158

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.

Homewood Suites by Hilton Chicago Downtown South Loop

Starting at $171

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.

Homewood Suites by Hilton Chicago Downtown West Loop

Starting at $196

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.

LondonHouse Chicago, Curio Collection by Hilton

Starting at $288

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Omni Chicago Hotel

Starting at $250

Escape and Save, Special Rates!
Book now and save up to 20% off with cancellations allowed at 48 hours prior to arrival. Any cancellation within 48 hours will require a forfeit of 1 night's room and tax.
Semi-Flexible Rate, book now!
Book now and save with cancellations allowed at 120 hours prior to arrival. Any cancellation within 120 hours will require a forfeit of 1 night's room and tax.
Special Rate, Advanced Purchase
Book now for your advanced trip and save! These rates are non-cancellable and non-refundable.

Palmer House a Hilton Hotel

Starting at $314

Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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The Drake Hotel, A Hilton Hotel

Starting at $210

Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
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Waldorf Astoria Chicago

Starting at $670

Best of Waldorf
Enjoy a $50 daily credit if you stay two or more nights.
Dream Away
Up to 15% off
Essential Traveler
Save Up to 15% Off. 4 night maximum stay.
Sweeten your Stay