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places to stay > United States > Chicago

Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works

Whether you are traveling to Chicago with your loved one for a special occasion (honeymoon, proposal or Valentine’s Day) or just on a romantic trip, here’s a list of Populer guesthouses that will more than satisfy any lovebird’s needs. In total exclusivity, discover our selection of the most popular guesthouses in Chicago.

Best places to stay in Chicago

Hyatt Regency O'Hare
Rosemont, Chicago
Bonfire Air Conditioning Free Shuttle Service Currency Exchange
Hyatt Regency
New East Side, Chicago
Spa Free Wi-Fi Bar Restaurant
La Quinta Inn & Suites
Chicago Loop, Chicago
Gym Laundry Service CCTV Electronic Keycard

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Top neighborhoods in Chicago

Streeterville

Streeterville is a neighborhood in the Near North Side community area of Chicago, Illinois, United States, north of the Chicago River. It is bounded by the river on the south, the Magnificent Mile portion of Michigan Avenue on the west, and Lake Michigan on the north and east, according to most sources, although the City of Chicago only recognizes a small portion of this region as Streeterville.

River North

River North is a lively neighborhood in the Near North Side. It boasts luxe shops and eateries, plus posh nightclubs and cocktail bars. Opened in 1930 in a former industrial area, the sprawling Merchandise Mart attracts throngs of shoppers to its home and office design showrooms. Surrounding the Mart, artist's studios in converted warehouses and lofts form a hub that sustains the area's foremost art galleries.

Gold Coast

The Gold Coast is a metropolitan region south of Brisbane on Australia’s east coast. It's famed for its long sandy beaches, surfing spots and elaborate system of inland canals and waterways. It’s also home to theme parks such as Dreamworld, Sea World and Wet’n’Wild. Inland, hiking trails crisscross Lamington National Park’s mountain ridges and valleys, home to rare birds and rainforest.

A world of choice

From a room for a night to a loft for as long as you like, there’s a Sonder for every occasion.

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7+ nights

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FAQ

1. What is The Hotels Fare?

The Hotels Fare offers a variety of unique spaces in 40+ cities around the world. Choose from stylish rooms and suites to spacious, five-bedroom apartments. With the The Hotels Fare app, everything is a tap away: self check-in, neighborhood guides, 24/7 support, and more.

2. If I need to cancel my reservation, will I receive a refund?

The Hotels Fare offers flexible cancellations for all bookings. Select the Flex Rate to cancel your booking up to three days before check-in and receive a full refund. For longer stays that are paid monthly, we require at least 30 days notice to cancel or modify without fees.

3. What are the top-rated vacation rentals for weekend getaways in Chicago?

An upscale neighborhood known for classic brownstones, luxury living, and proximity to Lake Michigan

4. What is the best part of Chicago to stay in?

River North is a great, bustling neighborhood for younger people who want to feel like they’re in the midst of the action. This neighborhood, which sits along the Chicago River, is a popular option because of its proximity to the Loop and its centralized location.

5. How many days should I spend in Chicago?

Four to five days in Chicago will allow you to see the major attractions. Make sure to give yourself some breathing room, especially if you plan to squeeze in some excursions.

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