Chicago, IL 4 Day Itinerary

Hotel Recommendations

Sofitel Chicago Magnificent Mile

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Great little neighborhood, just off of Michigan Ave and the lakeshore. Rooms are clean and spacious.

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The Ivy Hotel

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Clean and modern rooms, often set at an affordable price

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Thompson Chicago, by Hyatt

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A luxury boutique hotel in a great location, just off of the lakeshore.

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Virgin Hotels Chicago

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This hotel is modern and fun, with a great rooftop bar.

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The Godfrey Hotel Chicago

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This consistently affordable hotel is a great budget-friendly find. Clean and modern rooms.

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Food Recommendations

Hugo's Frog Bar & Fish House

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This is a sister restaurant to Gibson's Steakhouse next door, and home to the most incredible crab cake. While the Gibsons steaks are still on the menu, the fish and seafood options the specialty. Food and service are always top notch.

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The Purple Pig Restaurant

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Known for small plates, this restaurant has a varied menu with Italian, Greek and Spanish influences. The fresh pasta is some of the best in the city.

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Small Cheval- Riverside

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A grab and go version of the renown Au Cheval, this casual dining spot has the most amazing burgers and fries.

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Blue Door Kitchen & Garden

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This farm to table restaurant was created by executive chef and co-owner Art Smith, the former personal chef for Oprah. The food is consistently great, with charming decor and relaxing outdoor seating.

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Wildberry Pancakes & Cafe

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Everything is good here, especially can't go wrong with the berry bliss pancakes and any of the skillets.

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Bavette's Bar & Boeuf

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A classic steakhouse with a bit of a French flair. This restaurant is pricey but worth every penny. Great for a celebratory dinner as this place truly feels special. Reservations highly recommended.

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Billy Goat Tavern (The Original)

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This recommendation is really more a fun place to see than a foodie destination. Around since 1934, the restaurant was featured in a classic SNL skit- "Cheezborger, cheezborger, cheezborger!" The menu has stayed fairly simple and affordable.

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Garrett Popcorn Shops

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Try the Chicago mix, which is a combination of the caramel and the cheese popcorn. Locations all over the city

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Day One

Start your Chicago trip with a river boat cruise, learning the history and architecture of the city. Spend some time exploring Millennium and Maggie Daley Park, finishing off the day with a sunset walk along the lakeshore.

Shoreline Sightseeing

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Learn the history of the city through an architecture tour along the river. Take a nighttime cruise on a Wednesday or Saturday during the summer to watch the fireworks at the end of the tour.

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Millennium Park

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Famous for "The Bean" for a unique photo opportunity. Lots of concerts and special events take place here, so be sure to check out their calendar of events.

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Maggie Daley Park

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Adjacent to Millennium Park, Maggie Daley has a number of fun activities and areas to enjoy.

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Lakefront Trail

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The best skyline views are from the lake shore. You can get to this trail by taking an underpass from Michigan Avenue. A good place to start is the underpass near the gazebo by the Drake hotel.

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Day Two

Spend the day learning about natural history at the Field museum. (The Shedd Aquarium and Art Institute of Art are also great alternatives.) Next, enjoy the green space of Grant Park, or check out some shopping on Michigan Avenue. In the evening, take in one of the shows running in the theater district.  

Field Museum

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From Egyptian mummies to SUE, the most complete Tyrannosaurus rex ever discovered, the Field museum is a great option for any natural history fans.

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Grant Park

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Home to one of the largest fountains in the world, Buckingham Fountain. Each hour, a twenty minute water display reaches heights 150 feet in the air.

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Michigan Avenue

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With shops lining the street, including tucked away malls, Michigan Avenue has you covered if shopping is your goal.

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Broadway In Chicago

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With so many shows to choose from in the theater district, choose a show that best fits your group. They will not disappoint.

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Day Three

A more budget friendly day with a neighborhood feel. Spend the day around Lincoln Park Conservatory and Zoo, followed by a night out at the Second City comedy club. 

Lincoln Park Conservatory

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Built in 1877, the conservatory and surrounding gardens are free to enjoy but reservations are required.

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Lincoln Park Zoo

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This zoo has been completely free since its opening in 1968. With over 200 different species, expansive gardens, and conservation efforts, this is well worth a visit.

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The Second City

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This improv comedy club is where some of the most famous comedians got their start- Bill Murray, Dan Aykroyd, Steve Carell just to name a few. There is an age limit of 13 and up. Children between 13-17 must be accompanied by an adult.

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Day Four

Spend the day in the West Loop, starting at a unique spa experience, followed by a fun game of mini golf, ending the day with a movie at an outdoor rooftop cinema.

AIRE Ancient Baths Chicago

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Housed in a historic industrial building, enjoy some time at the baths. This spa designed as the ancient baths of Roman times, offers a number of different pools, saunas, salt baths, cold plunges and more.

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Puttery

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This can be an especially great option on a cold or rainy day, with a well-themed indoor mini-golf course and bar.

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Rooftop Cinema Club Fulton Market

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Watch a movie among the lights of the city in a cozy Adirondack chair at this outdoor cinema

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