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Bucket List

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.



360 family shot

360 Chicago

Magnificent views on the Magnificent Mile with a daring option to Tilt over the street below

wendella sightseeing lucia

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 Chicago Attractions

Art Institute

Founded in 1879, this Chicago treasure is one of the nation’s oldest and largest art museums

Chicago Architecture Center Sights museums

Chicago Architecture Center

The city’s starting point for all things architecture, design and history

chicago's first lady architecture river tour

chicago's first lady

The official architecture river tour of the Chicago Architecture Center

Skydeck Chicago Ledge attractions

skydeck chicago

Featuring spectacular views spanning up to four states and The Ledge for those who dare

Museum of Science and Industry Chicago sights museums

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 ferris wheel

navy pier

Chicago’s lakefront treasure is where you will find restaurants, rides and much more

Points of Interest

Franklin Tap Chicago Beer Dining Restaurant

Fort Dearborn

At the intersection of Michigan Ave. and Wacker Dr. and originally built in 1803 as a military fort

Historic Water Tower Points of Interest

Historic Water Tower

This treasured landmark is one of the few surviving structures from the Great Chicago Fire of 1871

Merchandise Mart point of interest

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 Chicago Point of Interest

Picasso Sculpture

This untitled sculpture by Pablo Picasso is located in the Loop’s Daley Plaza

chicago buckingham fountain

buckingham fountain

One of Chicago’s most notable icons can be found in Grant Park – bring pennies!

Monk's Pub Chicago Beer Dining Restaurant

Water Crib

These unique offshore structures protect water intakes that supply drinking water to the city


Take a walk at the rivers edge and experience the majesty of Chicago’s architecture and history

South Branch Chicago Beer Dining Restaurant

kinzie street bridge

This instagram friendly spot with an incredible views fshowcases a continuously raised bridge


Au Cheval, Chicago Food

Au Cheval

Considered the gold-standard of Chicago burgers, this place has the lines to prove it

garret-popcorn food

Garrett Popcorn

Plain, cheese, caramel crisp or the Garrett Mix, you will be hooked from the first bite

Gibson's food


Chicago’s classic Steakhouse that comes with a generous side of people-watching

Lou Malnatis Chicago food

Lou Malnati's

Using the freshest ingrdients possible is what makes their pies truly memorable

Minghin Chicago Asian Dining Restaurant

Weiners Circle

This long-standing late night joint sevres classic burgers and dogs with a hefty side of sass 

Mr. Beef Chicago Food

Mr Beef

The better burger alternative invented right here in Chicago – make sure to get it dipped


chicago blues bar kingston mines

Kingston Mines

Head to Lincoln Park for the city’s oldest and largest continuously running blues club with two stages

Club Lucky Chicago bar

Club Lucky

Vodka or Gin? Either way, this Bucktown gem serves the best martini’s in Chicago

Butch McGuires Chicago bar

Butch McGuire's

Grab a beer or cocktail – or three, at this classic and raucus Division Street imbibing institution

old Town Chicago Bars

Old Town Ale House

This shot and a beer drinking joint has been an Old Town favorite for over 50 years

Revolution Chicago Bar

Revolution Brewing

Beer aficionados will appreciate the selection of ales, stouts and sours

Delilah's Chicago Beer Bar


This Lincoln Park spot is hands down the city’s best bourbon bar

Three Dots and a Dash - Tiki Bar

Three Dots and a Dash

A Speakeasy tiki bar with 200+ rums & luau bites in a retro Polynesian-island setting

London House Chicago Bars

London House

Three chic levels of drinking & dining with spectacular sweeping city views


Franklin Tap Chicago Beer Dining Restaurant


This quaint North side neighborhood specializes in locally owned establishments

Historic Water Tower Points of Interest

Armitage Street

A lincoln Park shopping destination for many years will bring out the urbanite in you

Michigan Avenue Chicago Shopping

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

Picasso Sculpture Chicago Point of Interest

State Street

Like the song says, State Street that great street is home to hundreds of cool businesses

Wicker Park Chicago Shopping

Wicker Park

This hipster haven is a fun place to spend a few hours  shopping, drinking and dining