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Wildberry Pancakes & Cafe ($$)
130 E Randolph St, chicago
Established in 2004, Wildberry Café continues to delight guests with delicious dishes and welcoming hospitality. Their breakfast and lunch menus are inspired by a blend of traditional homemade recipes prepared to please the patron's taste. They use only fresh, seasonal ingredients that deliver the most delicious flavors and rich goodness.
- 0.8 MILES
- 19 minutes
- Get Directions
- 6:00am
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1.0-2.0 hr stay
Willis Tower Skydeck ($$)
233 S Wacker Dr, chicago
Willis tower, formerly the Sears Tower, is a 110-story skyscraper, and this skyscraper is Chicago's most dominant structure and 2nd tallest building in the Western Hemisphere. On a clear day, one can see approximately 40-50 miles (65 - 80 kilometers), allowing one to easily see four states – Illinois, Indiana, Wisconsin, and Michigan. Skydeck has a ledge glass box extending 4.3 feet from the Skydeck, providing a clear view of 1,353 straight down.
- 0.9 MILES
- 22 minutes
- Get Directions
- 6:00am
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Xoco ($$)
449 N Clark St, chicago
Xoco—pronounced "SHO-ko"—is the Aztec word for "little sister." Rick Bayless, who runs the iconic flagship restaurant Frontera, opened the place. But there's nothing little about Xoco's bold Mexican marketplace flavors. This quick-service café from Rick and Deann Bayless is open early and closing late and proffers contemporary expressions of Mexico's most beloved street food and snacks: flaky empanadas, hot-from-the-fryer churros, frothy Mexican hot chocolate, crusty tortas, and meal-in-a-bowl caldos.
- 0.8 MILES
- 19 minutes
- Get Directions
- 6:00am
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0.5-2.0 hr stay
Maggie Daley Park (Free Entry)
337 E Randolph St, chicago
Maggie Daley Park is a 20-acre magnificent recreation park offering a children's playground, a climbing wall, mini golf, picnic groves, a skating ribbon, tennis courts, roller blades, Micro Scooters & Bungee, and a formal garden. It also hosts a popular summer day camp. The park is named in honor of Maggie C. Daley (1943 – 2011), Chicago's longtime first lady, who was deeply committed to improving the lives of children and making the city culturally rich for all its citizens.
- 0.3 MILES
- 7 minutes
- Get Directions
- 6:00am
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0.75-2.0 hr stay
Chicago Lakefront Trail (Free Entry)
Lakefront Trl, chicago
Chicago's 18-mile-long scenic Lakefront Trail is an 18-mile-long stretch that extends from Ardmore Street on the North Side to 71st Street on the South, connecting to great neighborhoods, parks, and beaches. The trail passes through Edgewater, Uptown, Lakeview, Lincoln Park, South Loop, and Hyde Park neighborhoods. Each neighborhood offers its own unique experiences and a lot of things to do. Visitors and locals enjoy walking, running, biking, and rollerblading on the trail. Popular places on the route include south park shore, Jackson park, promontory point, 31st street harbor, northerly island, grant park, Maggie Daley park, Ohio Street beach, North Ave beach, Lincoln Park zoo, Belmont harbor, Montrose beach, and Foster Beach.
- 4.6 MILES
- 110 minutes
- Get Directions
- 6:00am
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Chicago Diner ($$)
3411 N Halsted St, chicago
Chicago Diner has been serving innovative and delicious vegan and vegetarian fare since 1983. True to their signage, "meat free since '83," all of their menus are a take on the classic American diner with a twist. It has earned numerous accolades from various media outlets for its fantastic food. They use local, seasonal ingredients and produce. All their cleaning products are eco-friendly, to-go containers are bio-degradable, and they practice bio-diesel conversion of waste oil.
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Lula Cafe ($$)
2537 N Kedzie Blvd, chicago
Lula cafe at Logan Square is inventive, market-driven, primarily organic food in a casual, funky space, hosting a trendy breakfast/brunch. They specialize in using locally sourced fresh produce and seasonal ingredients, and the patio is lovely on a warm night with the perfect atmosphere.
- 4.7 MILES
- 113 minutes
- Get Directions
- 6:00am
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0.5-1.0 hr stay
John Hancock Building & 360 Chicago ($$)
875 N Michigan Ave, chicago
360 Chicago is an observatory located on the 94th floor of the historic John Hancock Center in the heart of downtown Chicago. It offers breathtaking views of the city and Lake Michigan from over 1,000 feet above the Magnificent Mile. Visitors can also experience "The Tilt" for an additional fee; a series of floor-to-ceiling windows slowly tilt outside the building to 30°. There is also a Bar (CloudBar) to enjoy a drink (or two) while overlooking the view.
- 0.7 MILES
- 17 minutes
- Get Directions
- 6:00am
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0.5-1.5 hr stay
Chicago Riverwalk (Free Entry)
Riverwalk, chicago
The 1.25-mile path from the lakefront to Lake Street, Chicago Riverwalk, is an open, pedestrian waterfront located on the Chicago River in downtown Chicago. It connects four distinct districts; The Confluence, The Arcade, The Civic, and the Esplanade, with many places to stop and relax, various tours, and food vendors. The riverwalk offers glamorous architectural views of the city and refuge from the city's hustle and bustle.
- 0.3 MILES
- 7 minutes
- Get Directions
- 6:00am
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Eggy’s Diner ($$)
333 East Benton Place, chicago
Eggy's, a contemporary diner, is more than just breakfast (though it does have an extensive egg-centric menu). The 60's inspired menu is full of items designed to give a home-cooked feel. Think pancakes, grilled cheese sandwiches, and burgers. But it has made national news for its crunchy French toast, featured on Travel Channel's "Food Paradise" as a can't-miss carby dish.
- 0.4 MILES
- 10 minutes
- Get Directions
- 6:00am
- 6:15am
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1.5-2.0 hr stay
Chicago Architecture River Cruise ($$)
112 E. Wacker Drive, chicago
Chicago's riverboat architecture tours are well known among visitors and locals alike. The 90-minute tour discusses more than 50 famous historic and modern landmarks, including Willis Tower, Navy Pier, the Wrigley Building, Tribune Tower, Merchandise Mart, Lyric Opera, 333 West Wacker, Marina City, and many more. The tour guide also tells the fascinating stories of how a small settlement grew into a world-famous Chicago city.
- 1 MILES
- 24 minutes
- Get Directions
- 6:00am
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1.0-3.0 hr stay
Navy Pier (Free Entry)
600 E Grand Ave, chicago
Chicago's lakefront treasure, Navy Pier, is 50 acres of unparalleled attraction space. Nearly nine million people visit Navy Pier annually, making it the most visited attraction in Illinois and the Midwest. There are many indoor and outdoor attractions at Navy Pier, such as Chicago Shakespeare Theater, Chicago Children's Museum, impressively large Centennial Wheel, Carousel, Drop Tower, Navy Pier Beer Garden, and many more. You will also find shops, eateries, and theatres.
- 3.7 MILES
- 89 minutes
- Get Directions
- 6:00am
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Pequod's Pizza ($$)
2207 N Clybourn Ave, chicago
Pequod's Pizza has gained a cult following for its pan-style deep dish Pizza with a caramelized crust edge. The Pizza gained popularity with word of mouth, and Pequod's became the best-known secret for Pizza in Chicago. Mozzarella cheese is cooked along the edge of a cast-iron pan creating a crust unlike any other hence the name "caramelized crust." Customers get blown away after tasting the pie with the savory sauce and flavorful toppings.
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Beatrix ($$)
519 N Clark St, chicago
Chef partners Susan Weaver, Rita Dever and John Chiakulas have created a menu inspired by food made in Lettuce's test kitchen. Beatrix is open daily for breakfast, lunch, dinner and late night offerings. All pastries and sweets are baked in house daily. It features Modern, all-day venue combining an American eatery, wine & cocktail bar & a bakery/cafe. They offer the kale juice, mushroom burger, kale salad, steak and eggs and a side of granola, and veggie burger. They also have amazing Caramel pie for dessert. They have a lot of the same vendors as the Kane County flea market, but have some city based vendors as well. The items for sale range from bookshelves to vintage Ferragamo shoes. It is a very entertaining location, great people-watching out the wall of windows. The cocktail menu is refreshing and unique, appetizers are light and flavorful, and their entrees were superbly executed.
- 4.8 MILES
- 115 minutes
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0.5-1.0 hr stay
The 606 (Free Entry)
1805 N Ridgeway Ave, chicago
The 606 is a former elevated rail line, the Bloomingdale Line, converted into a combination walking, jogging, and biking path from Ashland Avenue to North Ridgeway Avenue. The trail connects to ground-level neighborhood parks, an observatory, art installations, and other amenities. There is a lot to see architecturally, lovely plantings along the way, with many entrances and exits along the route.
- 2.2 MILES
- 53 minutes
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1.0-2.0 hr stay
Wicker Park (Free Entry)
N Damen Ave & N Milwaukee Ave, chicago
Wicker park is famous for being an artsy neighborhood that always has something cool going on. There is something for everyone, including unique shopping places, trendy restaurants, coffee houses, and bars. The neighborhood is home to the historic victorian style homes built between 1873 and 1903.
- 2.6 MILES
- 62 minutes
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Southport Grocery and Cafe ($$)
3552 N Southport Ave Ste 1, chicago
Specialty grocery-cafe fusion place uses local ingredients to create artisanal culinary dishes, lunch boxes, ready-to-cook food, and gift baskets serving breakfast and lunch all day. They showcase numerous local food artisans. Customers come here to experience the from-scratch fare and unique dishes, including the occasional secret supper.
- 1.6 MILES
- 38 minutes
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1.0-2.0 hr stay
Green Mill Jazz Club (Free Entry)
4802 N Broadway St, chicago
Known for its jazz and poetry performances, this oldest continuously running jazz club in the U.S. opened in 1907. The bar still has the same sitting as it was 100 years ago. There's plenty of room for dancing to the fantastic live music. the Green Mill has appeared in many films. They have some excellent cocktails, and the live music is always good. The place is filled with lots of mob history in Chicago; Al Capone had a dedicated booth.
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Smoque Bbq ($$)
3800 N Pulaski Rd, chicago
Since opening in Chicago's Old Irving Park neighborhood in late 2006, Smoque has garnered a large and loyal following of locals and visitors alike, BBQ devotees. They have been consistently ranked among Chicago's best restaurants and the nation's best BBQ spots, winning many awards along the way.