1. Third largest city in the United States

The name ‘Windy City’ may be known throughout the world but the fact that Chicago is the third largest city in the United States may not. Trailing only a few short steps behind New York City and Los Angeles, Chicago enjoys a rising number of tourists from all around the world, with 55 million visitors last year, a consistently-growing number compared to the years before.

Millennium Park, without a smidgen of doubt, managed to hang onto its top spot as the most visited attraction in downtown Chicago. In fact, its record is unbeaten throughout the Midwest. The city also has a large number of other similar attraction that emits the same gravitational pull – The Art Institute of Chicago, Cloud Gate, Willis Tower, Navy Pier, Shedd Aquarium, Chicago History Museum and Lincoln Park Zoo, the Grant Park Music Festival, Chicago Opera Theater events and Harris Theater for Music and Dance, just to name a few.

The list of popular tourist attractions may continue to be the biggest draws to Chicago, but so are the countless types of unique cuisine and shopping destinations. Don’t miss the chance to hunt down exclusionary and delicious Chicago-style hot dogs, deep dish pizza or the Maxwell Street Polish Sausage while taking the charter bus around intriguing architectural structures like Sears Towers and museums that feature 1920s gangster history like Al Capone, Frank ‘The Enforcer Nitti’ (Al Capone’s successor), John ‘Papa Johnny Torrio, John Dillinger, Lester Joseph ‘Baby Face’ Nelson, etc. And when you’re ready for some serious shopping, organize a few side trips to Magnificent Mile or State Street. The streets are lined with famous branded retail outlets, family-run shops, fanciful diners, fast food restaurants, playful cafes, bakeries, breezy ice-cream shops and coffee outlets.


  • Millennium Park 201 E Randolph St, Chicago, IL 60602 (312) 742-1168
  • Art Institute of Chicago 111 S Michigan Ave, Chicago, IL 60603 (312) 443-3600
  • Willis Tower 233 S Wacker Dr, Chicago, IL 60606
  • Navy Pier 600 E Grand Ave, Chicago, IL 60611 (312) 595-7437
  • Shedd Aquarium 1200 S Lake Shore Dr, Chicago, IL 60605 (312) 939-2438
  • Chicago History Museum 1601 N Clark St, Chicago, IL 60614 (312) 642-4600
  • Lincoln Park Zoo 2001 N Clark St, Chicago, IL 60614
  • Harris Theater 205 E Randolph St, Chicago, IL 60601 (312) 334-7777


2. The Country’s Railroad Capital

With well over 1,300 trains ferrying people in and out of the capital, into and out of suburbs, The Loop, and boasting of the world’s very first elevated railway, getting in and around Chicago is a breeze. Chicago is also an easy-to-navigate city, with predictable north and south boundaries, and east and west divide, all cut up into grids. The ‘L’, short for the Loop, and its elevated railway was amazingly designed and constructed during a period of time when no such precedent was yet set. It was built in 1892 and mobilizes more than 1.7 million passengers on a weekly basis, connecting the city both above and below ground through 144 rail stations all over town. The Blue Line and The Red Line operates 24 hours a day between the north and south of Chicago downtown; the Metra, a high-speed commuter train, is used to ferry people in and out of some outlying suburbs.


Traveling alone or with a couple of friends, the CTA Visitor Passes, which has a set number of admission days loaded into the cards, is more than enough to get you around. It costs $10 to $105 for 1 to 30 days of rides. If you’re unsure about how much moving around you’ll be doing, get the unlimited ride options. The good news is that the passes can be ordered and delivered ahead of time! Load your preferred amount into your Ventra card, personal bankcard, or get disposable 1-day tickets which can be purchased from Ventra Vending Machines all around town and you’re good to go!

For tourists who would like to have a look-around Chicago while on-the-go, catching a Water Taxi or renting a bicycle will also get you places. The Water Taxis offers a great combination of a sightseeing tour around popular Chicago museums, Chinatown, Willis Tower, Union Station, Michigan Avenue (and many more) and lets you languidly explore these amazing sites without stretching yourself too thin.


  • Chicago Water Taxi stops Ogilvie/Union (West Loop), Michigan Avenue Stop, LaSalle (River North), Riverwalk Clark Street, Chinatown, Chicago Avenue, North Avenue/Sheffield
  • Unlimited Ride Passes
  • Bike and Roll Chicago – Navy Pier 700 E Grand Ave, Chicago, IL 60611 (312) 729-1000
  • Bobby’s Bike Hike 540 N Lake Shore Dr, Chicago, IL 6061 (312) 245-9300
  • Wheel Fun Rentals 305 East Riverwalk, Chicago, IL 60611 (773) 458-0868
  • Divvy 33 S Michigan Ave, Chicago, IL 60601 (855) 553-4889


3. Chicago Is a Breath of Fresh Air

With more than 8,000 acres worth of green space in the form of 26 beaches and 580 parks around town, Chicago provides you with enough space for a calming respite if you fancy a day of complete quiet. Some of the parks can be found not too far from downtown Chicago, with some built right into its heart, while others are easily accessible with both private and public transportation. The city is also well-connected by bike lanes for those who prefer to wheel their way around. With 225 miles of lanes, 13,000 bike racks, 3,000 bikes and 300 bike stations through the Divvy bike-sharing system alone, most notable attractions and iconic landmarks of Chicago is literally a cycle away.


You can enjoy events around Lake Michigan and Grant Park with free admission into Jay Pritzker Pavilion, Cloud Gate and the Crown Fountain at Millennium Park, visit the notable fieldhouse and let the kids loose at Indian Boundary Park which are regular stomping grounds for local health enthusiasts. Soak in the pristine landscape, natural formations, stone paths, and Midwest-themed Columbus Park, or bring the rented charter bus to Chinatown of Chicago where Ping Tom Memorial Park is strategically located. As water taxis connect two of the abovementioned parks to the city center, you’re still just a stone’s throw away from all the buzz when night falls.

You can also chill out and enjoy the serene scene of Chicago from North Avenue Beach, go bird-watching or let the kids play in the playground of Lane Beach, enjoy the hidden beach of Rainbow Beach, and if you’re visiting with your furry friends, head over to Belmont Harbor Dog Beach where they can prance around in absolute delight to their heart’s’ content.


  • Indian Boundary Park 2500 W Lunt Ave, Chicago, IL 60645 (773) 764-0338
  • Columbus Park 500 S Central Ave, Chicago, IL 60644 (773) 287-7641
  • Ping Tom Memorial Park 1700 S Wentworth Ave, Chicago, IL 60616 (312) 225-3121
  • North Avenue Beach 1600 N Lake Shore Dr, Chicago, IL 60613 (773) 363-2225
  • Lane Beach 5915 N Sheridan Rd, Chicago, IL 60660 (773) 363-2225
  • Rainbow Beach 2873 E 75th St, Chicago, IL 60649 (312) 729-1000
  • Belmont Harbor Dog Beach N Lake Shore Dr & Lake Shore Drive Dr, Chicago, IL 60657 (312) 742-7529

4. The Impressive Historical Side of the Windy City

The first permanent resident of Chicago was an African-American businessman from what is now Haiti, Jean Baptiste Point du Sable, in 1779. Here, du Sable built his home with his Indian wife and the rest, as they say, is history. Visitors are encouraged to stop by either Chicago History Museum, Newbury Library or the Clarke House Museum to browse through the countless documents, artifacts, pictures, maps, magazines, newspapers, and directories. These are real-life stories about the Great Chicago Fire, pictures and documents related to the unique world of Chicago architecture, history of railroads by The Pullman Company, the Illinois Central, and the Chicago, Burlington & Quincy. It doesn’t more real than this! Troop your way around The Clarke House Museum you, the oldest house in town, with the free hourly your on Wednesday, Friday or Saturday.



  • Chicago History Museum 1601 N. Clark St., Chicago, IL 60614 (312) 642-4600
  • Newberry Library 60 W. Walton St., Chicago, IL 60610 (312) 943-9090
  • Clarke House Museum Chicago Women’s Park, 1827 S. Indiana Ave. Chicago, IL 60616

5. Of Art and Eating

If a hot dog was an art, you’d never run out of options. Boasting of well over 2,000 hot dog stands located within the sprawling Chicago downtown area and its quaint suburbs, a long list of award-winning chef-owned restaurants and diners and a conglomeration of affordable cheap eats, Chicago is a foodie haven in every sense of the word. Together, the army of hot dog stands collectively outnumber the Burger Kings, McDonalds and Wendy’s of Chicago. So, don’t be surprised to learn that the first McDonald’s in the United States made its mark with the first restaurant in Chicago in 1955. Chicago-style pizza made a splash in the dining scene when Pizzeria Uno opened its doors in 1943.


With its culinary offerings come its large collection of impressionist paintings. Housed in The Art Institute of Chicago, it remains to be the largest collection of its kind outside of Paris, France. The art institution is known and globally-recognized for its active curational efforts as it brings in and hosts a large variety of paintings, sculptures and historical artifacts from all around the world, drawing more than 1.5 million patrons and participants every single year. The art institute is also connected with the famous, historic Route 66, by marking its starting point. The Main Street of America or Mother Road, as Route 66 is fondly referred to, has become world-famous thanks to its expansiveness (measuring near 4,000 km in total) via the hit song and television show of the same name. Even to this very day, the Mother Road is considered a major work of art.


  • Art Institute of Chicago 111 S Michigan Ave, Chicago, IL 60603 (312) 443-3600
  • Hot”G”Dog 5009 N Clark St, Chicago, IL 60640 (773) 209-3360
  • Jimmy’s Red Hots 4000 W Grand Ave, Chicago, IL 60651 (773) 384-9513
  • Chicago’s Dog House 816 W Fullerton Ave, Chicago, IL 60614 (773) 248-3647
  • The Wieners Circle 2622 N Clark St, Chicago, IL 60614 (773) 477-7444

Although they’re not technically ‘secrets’ per se (is ANYTHING a secret these days, with the internet?), I think the short list and resource above will help you discover the important facades to Chicago. Some less touristy than others because of stuff like water taxis and hot dogs, as touristy as they are, are not to be missed! Visiting serene green spaces and beaches in Chicago is a way to help you find the sweet, serene spot when you need it.