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Chicago hotel rates are as temperamental as the city's climate. And just as snow in April and balmy weather in November are not uncommon, it is widely accepted that a hotel's room rates may drop $50 to $100 overnight—and rise again the next day. It all depends on the season and what festivals, conferences, and other events are happening around town.
Even so, it's wise to shop around. Focus on a neighborhood of interest, like the Near North Side, and you'll find budget chains such as Embassy Suites and luxury properties such as the Four Seasons Hotel Chicago within a few blocks of each other.
Ask yourself whether you'd rather be surrounded by the sedately dressed—think Trump International Hotel—or tattooed hipsters, à la the James Chicago. Is it romance you're seeking (try the Drake) or a quick weekend escape with the kids in tow (they can splash around the pool at the Radisson Blu Aqua, then walk a block to Millennium Park)?
On the lower end, expect well-maintained, but often boxy and sparsely decorated rooms. The good news is that free Wi-Fi is now a feature of most budget-friendly hotels, such as the Best Western or Holiday Inn chains, and local outfits like the Essex Inn.
Top-tier hotels have no problem filling their rooms: in some cases, this has little to do with amenities. Instead, their vibrant bar scenes are the draw, as is the case at the W Chicago–Lakeshore, W Chicago–City Center, the Wit, and the James Hotel. Rooms at these hot spots usually don't go for less than $250, but the "it" factor is huge. That said, between 2013 and 2015 the city saw a building boom that introduced some 2,700 new hotel rooms; the added competition may help lower prices and increase overall quality.
This historic property, built in 1895 by D.H. Burnham & Co. as one of the first skyscrapers, retains ornate original details including Carrara marble and wrought-iron-trimmed elevators. Rooms have historic charm (read: they're on the small side) but are comfortable, especially for the business traveler. There's also a great restaurant, Atwood, on-site that serves modern American food.
The atmosphere at this sleek spot, topped by ROOF, one of the Loop's most happening bars, is fun and youthful; the same can be said of the guest rooms, which are moderately sized and modern, with hanging wall art meant to resemble puckered lips. The hotel announces itself with a massive lightning bolt out front and winged lighting sculptures in the lobby. It's the perfect place to see and be seen; you'd never guess this is a Hilton property.
Named a National Historic Landmark in 1999, the Allerton was a residential, 12-story "club hotel" for men when it opened in 1924; the hotel added 14 more floors in 1930, making it the tallest building on Michigan Avenue at the time. The guest rooms have been remodeled with an attractive mix of blue, white, and yellow; new king and queen beds are an added bonus. If you want to stay in the middle of it all, this is a very good choice.
Designed in a slightly quirky French provincial style, the cozy lobby of this small boutique hotel with a 1920's-era vibe opens onto a tree-lined street in Lakeview. The Willows is just three blocks from the lake and central to Broadway Avenue boutiques, restaurants, and movie theaters. A prime location equally close to Lincoln Park and Wrigley Field makes it a great destination for a North Side stay.
Just blocks from the Wrigley Building and Tribune Tower, it offers impressive views of the Chicago River and the heart of downtown. Clean-lined, contemporary rooms are decorated in soothing neutral tones, and all have free Wi-Fi and iPod docks. There's also a business center and fitness center, so you can decide whether to work or work out. Hoyt's, the hotel restaurant, serves creative, Midwestern-inspired fare and has a whole menu section devoted to snacks in jars.
In an often overlooked section of Chicago just east of Michigan Avenue, this hotel has a sublime 29th-floor indoor/outdoor bar with an enviable view of the city; its stylish guest rooms are contemporary and comfy. The lobby, renovated in 2013, features oversize seating and opens to a restaurant and bar offering sit-down service as well as to-go items. This place loves kids and pets and has packages tailored to both.
