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Top tips for finding Chicago hotel deals
If you’re looking for a cheap hotel in Chicago, you should consider visiting during the low season. You'll find cheaper accommodations in Chicago in January and February.
Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Chicago if you stay on a Sunday. The opposite is true for, Monday, which is usually the most expensive day.
Book at least 90 days before your stay begins to get the best price for your Chicago accommodation.
How long should you stay? KAYAK users usually book their accommodation in Chicago for 0 days.
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
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.
Hotels in Lake View, West Town, and near Civic Opera House have the most searches on KAYAK.
Eurostars Magnificent Mile, River Hotel and Congress Plaza Hotel are very popular with users who want to stay within walking distance of Civic Opera House.
The average price of a double room in Chicago is R3 657, but it varies considerably depending on location, facilities, and seasonality. In the last 3 days, KAYAK users have found double rooms for as cheap as R425.
Hotels are safe environments for travellers as long as they properly implement sanitary measures in response to coronavirus (COVID-19). However, we recommend getting in touch with the local authorities regarding safety procedures for hotels in Chicago. For more advice, please view our information page on what to know about coronavirus (COVID-19) and travel.
After you launch a hotel search on KAYAK, you can refine your research by neighbourhood, which allows you to pick the central Chicago districts. You can also do a search using the city map to choose a specific location, like Chicago city centre
Take a look at our extensive hotel map to find the best hotels near you.
Where to stay in Chicago?
Our map will help you find the perfect place to stay in Chicago by showing you the exact location of each hotel.