Chicago Weekend Guide

The Chicago metropolitan area, located along beautiful Lake Michigan, is also known as Chicagoland, and it's home to almost 10 million people. The city is full of breathtaking architecture and landscaped public parks. Here's a quick guide for seeing the best of the Windy City in just 48 hours.

1. Hotel Burnham
Burnham Hotel
Kimpton Hotels and Restaurants

Built by Daniel Burnham in 1895, this charming boutique hotel in the historic Reliance Building, served as a model for our nation's first skyscrapers. The hotel is an architectural treasure with a prime location near Chicago's Cadillac Palace Theater and Ford Center for the Performing Arts. The rooms feature plush beds and the mahogany writing desks echo the motif of the wood-paneled lobby. Its history is enhanced with modern design and amenities like complimentary Starbucks coffee in the lobby each morning and a wine reception each afternoon from 5 to 6 p.m.

Bring your furry friends: pets are welcome at the Burnham and pet beds, treats, dog-walking and litter box cleaning services are available.

  • 1 West Washington Street
  • Chicago, IL 60602 US
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2. The W Lakeshore
The W Lakeshore
Starwood Hotels
The W hotels are synonymous with luxury, and Chicago's lakeshore location is no exception. This hip hotel offers plush rooms decorated in deep reds, black and gray -- a welcome break from the beige, sage and white in most other hotels. When booking, "wonderful rooms" feature dramatic city views and the pricier "spectacular rooms" boast lake views. Situated in the hotel is the trendy Wave restaurant and Rande Gerber, a stylish top-floor bar.

If you are a runner, you're steps from the scenic lakefront path; pamper yourself after your run at the Midwest outpost of the popular Bliss Spa.
  • 644 North Lake Shore Drive
  • Chicago, IL 60611 US
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3. The Majestic Hotel
The Majestic Hotel
This hotel is the perfect choice for those seeking a peaceful retreat rather than a stylish hot spot. The Majestic is located on a quiet tree-lined street near the restaurants and shops lining Lincoln Park. The larger suites in the hotel feature sun porches, butler's pantries, a refrigerator, microwave and a wet bar. If you plan on attending a Cubs game while in Chicago, this hotel is ideal as it's only a short walk to Wrigley Field.
  • 528 West Brompton Avenue
  • Chicago, IL 60657 US
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4. Where to Eat: MK
Jeff Schear
Foodies rank mk one of the best American restaurants in Chicago, and while the food truly is excellent, the restaurant is in no way pretentious. Chef Michael Kornick created a menu that's a seasonal mix of meat and seafood served in mk's understated loft-like dining room. There's something for everyone on the menu, and if you're ordering dessert, try the decadent and heavenly Peanut Gallery: peanut butter mousse, crispy milk chocolate, warm brownies, pretzels, hot fudge and caramel.
  • 868 N. Franklin
  • Chicago, IL 60610 US
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5. Where to Eat: The Chicago Diner
The Chicago Diner
Lonely Planet Images / Getty Images
Chicago offers some tasty options for vegetarians and vegans, too. The Chicago Diner is a haven of meatless dining, with a menu that features breakfast, lunch and dinner options. During the weekend brunch, definitely order the Hash and Tofu Scrambler: scrambled tofu, spicy tempeh, potato hash, vegan biscuits and gravy, and fresh fruit. Truly tantalizing to the vegan sect are their non-dairy desserts like black forest, cookies and cream or lemon cakes.
  • 3411 North Halsted Street
  • Chicago, IL 60657 US
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6. What to See & Do: Millennium Park
Millennium Park
Photographer's Choice / Getty Images
Just south of Michigan Avenue is Millennium Park, which opened in 2004. Chicago's parks are the city's pride and joy, and in Millennium, you can walk across the undulating bridge designed by Frank Gehry or stand beneath his silver "Bean" sculpture to see your own reflection against Chicago's skyline. You can also listen to a concert under his metallic band shell, a sophisticated outdoor space known as the Jay Pritzker Pavilion.

If you're visiting Chicago during the summer months, be sure to check out the Crown Fountain, which consists of two monoliths that project images of Chicagoans.
  • 201 E. Randolph St.
  • Chicago, IL 60602 US
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7. What to See & Do: Lakefront Esplanade
Lakefront Esplanade Bike Tour
Photographer's Choice / Getty Images
Jog, walk, bike, blade or skate along this beautiful walkway. The path is less crowded on the South Side and views around the museum campus are stunning. Museum Campus houses the Shedd Aquarium, Field Museum, Adler Planetarium and Soldier Field -- all tied together by beautiful lawn space perfect for an afternoon of sightseeing.

Enjoy an amazing guided lakefront bicycle tour as offered by Bike Chicago. Choose from options such as the Presidential tour, which travels past President Obama's childhood home, or the night tour, which tours Chicago's spectacular skyline and ends in a fireworks display.
  • Navy Pier 600 E. Grand Avenue
  • Chicago, IL 60611 US
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8. What to See & Do: Wrigley Field
Wrigley Field
Getty Images
Although the Cubs haven't made it to the World Series since 1945, taking in a game at Wrigley Field is an iconic American experience. The ivy-covered outfield walls and hand-operated scoreboard remind you why, win or lose, baseball is America's pastime. Tickets sell out fast so don't miss out. Hit a weekday game or try your luck on game day outside the park where season ticket holders will gather to unload a few seats.
  • 1060 West Addison Street
  • Chicago, IL 60613 US
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9. After Dark: Empty Bottle
Empty Bottle
Lonely Planet Images / Getty Images
Located on the corner of Cortez and Western in Chicago's Humboldt Park, the Empty Bottle has an old tavern atmosphere. In the evenings the extensive wine collection is complemented by an array of experimental jazz and rock bands in addition to some of Chicago's best DJs.
  • 1035 North Western Avenue
  • Chicago, IL 60622 US
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10. Improv Comedy
The Second City
The Second City
Second City is a legacy in the comedy business, producing such talents as John Belushi, Mike Myers, Bill Murray and Gilda Radner. If Second City is sold out, check out the improv of Neofuturists. The theater group bill themselves as a fun fusion of sports, poetry, comedy and living newspaper.
  • 1616 North Wells Street
  • Chicago, IL 60614 US
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