Chicago Trip Guide | Midwest Living

Chicago Trip Guide

Soaring observation decks and winding park trails show the Midwest’s biggest city in a whole new light.


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  • 1
    Willis Tower.
  • 2
    Seadog's Lake and River Architecture Tour.
  • 3
    Jay Pritzker Pavilion in Millennium Park.
  • 4
    Lincoln Park Zoo carousel.
  • 5
    Lakeshore trails.
  • 6
    Adler Planetarium. Photo Courtesy of Adler Planetarium.
  • 7
    The Field Museum.
  • 8
    Wrigley Field.
  • 9
    Atwood Cafe. Photo Courtesy of Atwood Cafe.

Where to stay

The Allerton Hotel Chicago Beyond its 1920s redbrick Renaissance exterior, the Allerton is contemporary. Rooms at this Magnificent Mile spot are comfortable with calming aesthetics. From $99. See reviews and ratings. (877) 701-8111;

Embassy Suites Chicago—Downtown/Lakefront A 10-minute walk from Navy Pier, the River North hotel recently completed a multimillion upgrade. From $159, including breakfast. (312) 836-5900;

Hard Rock Hotel Chicago Music fans love this salute to rock in the 1929 Carbide and Carbon Building on Michigan Avenue (musician memorabilia on display throughout the building). From $159. (866) 966-5166;

Holiday Inn Chicago Mart Plaza An affordable chain hotel in River North recently completed a $20 million ecofriendly renovation. Every room has a view and free Wi-Fi, a skywalk connects to the Merchandise Mart, and kids eat free. From $103. (312) 836-5000;

Hotel Allegro A renovated landmark in the Loop’s theater district blends vibrant colors with original Art Deco design. From $159. (866) 672-6143;

Hotel Felix The River North hotel combines a 1927 Beaux Arts building with contemporary furnishings. Sensors reduce energy usage when rooms are unoccupied. From $129. See reviews and ratings. (312) 447-3440;

Hotel Sax Chicago The high-energy, upscale hotel with a nightclub just off the lobby stands alongside the House of Blues in Marina City. From $179. (312) 245-0333;

Inn of Chicago Magnificent Mile You can walk just about anywhere from this hip boutique hotel in Streeterville. The 1920s facade complements sleek furnishings. Soak in the view from the 22nd-floor deck. From $149. (312) 787-3100;

JW Marriott Chicago A $396 million project has transformed a historical Burnham building into a luxe hotel. The property includes a 20,000-square-foot spa. From $229. (312) 660-8200;

Renaissance Blackstone Hotel A $128 million renovation breathed new life into the South Michigan Avenue hotel that once hosted presidents. From $189. (312) 447-0955;

Trump International Hotel and Tower Chicago Standard rooms at this shockingly pricey (but oh-so-luxurious) hotel have soaking tubs, a kitchen, fireplace and 10-foot window wall. Sixteen, on the 16th floor, serves dinner with a view. From $475. See reviews and ratings.  (312) 588-8000; 

The Wit Check-in includes a warm chocolate chip cookie, and throughout the hallways, you’ll hear the chirping of birds and crickets. In the Loop’s theater district. From $209. See reviews and ratings.  (312) 467-0200;

More information: Choose Chicago (312) 567-8500;




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