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You are going to need an awfully big bucket for all of the great things Chicago has in-store for first-time visitors to the Windy City. From an architecture cruise on the Chicago River or seeing your reflection in the “Bean” at Millennium Park to the addictive Garrett Mix and decadent deep-dish we encourage you to indulge in any (or all) of these incredible experiences.
Attractions/Tours
Museums
360 Chicago
Magnificent views on the Magnificent Mile with a daring option to Tilt over the street below
wendella sightseeing
No trip to Chicago is complete without an architectural river cruise, and this iconic family-owned tour company hits the mark
Art Institute
Founded in 1879, this Chicago treasure is one of the nation’s oldest and largest art museums
Chicago Architecture Center
The city’s starting point for all things architecture, design and history
chicago's first lady
The official architecture river tour of the Chicago Architecture Center
skydeck chicago
Featuring spectacular views spanning up to four states and The Ledge for those who dare
steve's segway tours
One of the best ways to see the city’s most iconic sights is aboard a fun segway
navy pier
Chicago’s lakefront treasure is where you will find restaurants, rides and much more
Points of Interest
Fort Dearborn
At the intersection of Michigan Ave. and Wacker Dr. and originally built in 1803 as a military fort
Historic Water Tower
This treasured landmark is one of the few surviving structures from the Great Chicago Fire of 1871
Merchandise Mart
This massive art deco structure was the largest building in the world when completed in 1930
Millennium Park
Chicago’s motto, urbs in horto “city in a garden” is personified at this lakefront crown jewel
Picasso Sculpture
This untitled sculpture by Pablo Picasso is located in the Loop’s Daley Plaza
buckingham fountain
One of Chicago’s most notable icons can be found in Grant Park – bring pennies!
Water Crib
These unique offshore structures protect water intakes that supply drinking water to the city
Riverwalk
Take a walk at the rivers edge and experience the majesty of Chicago’s architecture and history
kinzie street bridge
This instagram friendly spot with an incredible views fshowcases a continuously raised bridge
Dining
Au Cheval
Considered the gold-standard of Chicago burgers, this place has the lines to prove it
Garrett Popcorn
Plain, cheese, caramel crisp or the Garrett Mix, you will be hooked from the first bite
Gibson's
Chicago’s classic Steakhouse that comes with a generous side of people-watching
Lou Malnati's
Using the freshest ingrdients possible is what makes their pies truly memorable
Weiners Circle
This long-standing late night joint sevres classic burgers and dogs with a hefty side of sassÂ
Mr Beef
The better burger alternative invented right here in Chicago – make sure to get it dipped
Nightlife
Kingston Mines
Head to Lincoln Park for the city’s oldest and largest continuously running blues club with two stages
Club Lucky
Vodka or Gin? Either way, this Bucktown gem serves the best martini’s in Chicago
Butch McGuire's
Grab a beer or cocktail – or three, at this classic and raucus Division Street imbibing institution
Old Town Ale House
This shot and a beer drinking joint has been an Old Town favorite for over 50 years
Revolution Brewing
Beer aficionados will appreciate the selection of ales, stouts and sours
delilah's
This Lincoln Park spot is hands down the city’s best bourbon bar
Three Dots and a Dash
A Speakeasy tiki bar with 200+ rums & luau bites in a retro Polynesian-island setting
London House
Three chic levels of drinking & dining with spectacular sweeping city views
Shopping
Andersonville
This quaint North side neighborhood specializes in locally owned establishments
Armitage Street
A lincoln Park shopping destination for many years will bring out the urbanite in you
Michigan Avenue
The Magnificent Mile and home to dozens of national, luxury flagship brands
Oak Street
This small stretch of Haute fashion and expensive baubles is a high rollers dream
State Street
Like the song says, State Street that great street is home to hundreds of cool businesses
Wicker Park
This hipster haven is a fun place to spend a few hours shopping, drinking and dining