Chicago hotels

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Good to know

Low season	January
High season	October
Average price (weeknight):	S$ 312
Average price (weekend night):	S$ 313

cheapest month to stay

47%

expected price decrease

most expensive time to stay

31%

expected price increase

(avg. price over the last 2 weeks)

Sun - Thu

(weeknight)

(avg. price over the last 2 weeks)

Fri & Sat

(weekend night)

How much does a hotel in Chicago cost?

No. 1 most popular

The St. Clair Hotel - Magnificent Mile

S$ 103

No. 2 most popular

Travelodge by Wyndham Downtown Chicago

S$ 109

Best value

Ihsp Chicago Inn At Damen Cta

S$ 34

No. 1 most popular

Hilton Garden Inn Chicago Downtown/Magnificent Mile

S$ 153

No. 2 most popular

Holiday Inn Express Chicago - Magnificent Mile

S$ 122

Best value

Found Hotel Chicago River North

S$ 49

No. 1 most popular

The Peninsula Chicago

S$ 478

No. 2 most popular

Staypineapple, An Iconic Hotel, The Loop

Top tips for finding the perfect Chicago hotel

To be near Chicago’s best upscale shopping, stay near Magnificent Mile, a strip of Michigan Avenue that runs through the commercial heart of the city.
From mid-range hotels like the Warwick Allerton - Chicago to the upscale Sofitel Chicago, guests can find a range of hotel options in the Magnificent Mile area.
The Loop is Chicago’s business district. Home to both The Art Institute of Chicago as well as Grant Park, it boasts a variety of hotels for all budgets.
One of The Loop’s best business hotels is The Silversmith Hotel, which features four meeting rooms and a conference space. Kimpton the Gray is another exceptional option in this region.
For places to stay by Chicago Midway Airport, Skylark Motel is a decent option for those travelling on a budget. For mid-range accommodation, Holiday Inn Chicago Midway Airport and Hyatt Place Chicago Midway Airport are both good choices.
Chicago’s metro system, known as the L, connects Chicago O’Hare International Airport to the city centre via the Blue Line, reaching the city in just under an hour. Those seeking a convenient transfer to the airport should look for hotels along this line.
For a picturesque stay on Michigan Avenue consider Congress Plaza Hotel or Chicago’s Essex Inn. Both hotels offer views of Lake Michigan and Grant Park.
Families may enjoy staying at the Sheraton Grand Chicago, just a short walk from the amusement park rides and restaurants of Navy Pier, the Children’s Museum, and Ohio Street Beach.

FAQs when booking a hotel in Chicago

Hotels near Grant Park have the most searches on KAYAK.

Travellers who like staying near Grant Park recommend Congress Plaza Hotel, Palmer House a Hilton Hotel, and Hilton Chicago.

KAYAK users have found double rooms in Chicago for as cheap as S$ 14 in the last 3 days. The average price is S$ 317.

More affordable accommodation can be found in the southern part of the Loop, known as Painter’s Row, as well as in the northern parts of the city like Old Town and Gold Coast. Across the river, Chicago Parthenon Hostel is a good option for budget travellers as is Chicago Getaway Hostel near Lincoln Park.

Yes, many hotels on Chicago’s North Side accept dogs and other pets, including Waldorf Astoria Chicago on the Magnificent Mile, and the nearby Dana Hotel and Spa. Guests staying at Hotel Lincoln can take their dogs for a walk in Lincoln Park, a vast city park on the edge of Lake Michigan.

The Peninsula Chicago is renowned for its Sunday brunch, but also offers an excellent daily breakfast. For a very good breakfast buffet, included with the price of your room, book a stay at Embassy Suites Chicago Downtown. Made-to-order omelettes, french toast, pancakes, bacon, sausage, and a variety of fresh fruits round out the package.

Yes, however, hotels in Chicago that offer free parking are located in the outskirts of the city. About 4 mi outside the city centre, The Hotel at Midtown in the Bucktown neighbourhood is a good option. Those flying out of Chicago Midway Airport will enjoy the convenience of Carlton Inn Midway or Chicago Lake Shore Hotel.

In the last 3 hours, users have found Chicago hotels for tonight for as low as S$ 16. Users have also found 3-star hotels from S$ 36 and 4-star hotels from S$ 124.

Search here to find similar prices.

In the last 72 hours, users have found Chicago hotels for this weekend for as low as S$ 19 per night. Users have also found 3-star hotels from S$ 97 and 4-star hotels from S$ 125.

Search here to find similar prices.

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