Chicago is one of the beautiful cities and must-visit places in the world with its diverse culture and elegant architecture with loads of fun to offer for several days. Located in the Mid-West of the United States of America along Lake Michigan, it is known for its adverse weather conditions and is also called Windy City (well may not be for the weather but due to politics) One would understand it better while flying in Winter (which is usually October to May) thru O’hare, Chicago’s international airport due to numerous cancellations of flights or long delays. But that shouldn’t stop visiting O’hare and Chicago and this should help you explore like a local.

Named after a local crop chicagoua which is nowhere to be seen now, it is third most populated with amazing sweet people all around willing to help/talk, unlike New Yorkers, no offense 😛 Obviously, one can find many more stats in Wikipedia, but if one visiting and looking for the best places to look around and eat, this should be your Wiki.

With that said, let’s dive into the world of Chi-Town.

After the tiresome flight, I am sure one needs to lie flat soon and if you are looking for a bed close to the airport and quick transport to downtown, Rosemont is the best and safe neighborhood with reasonable prices. The bonus, you are close to The Fashion Outlets of Chicago, Convention Center, movie theatres, and the one and only popular blue line which takes us to the heart of Chicago Downtown, The Loop. Parking is not that bad Downtown but why miss a chance to travel like a local experiencing spectacular Skyline view and Chi-rail system, right?

Enjoy the architecture capital of the United States.

Skydeck Chicago in clouds
Backdrop –  Willis Tower amid the fog


John Hancock Center: 

Fourth tallest in the town, 100 storeyed black X framed tower is a must-visit than regular Sears Tower for its breathtaking views of Lake Michigan, Lakeshore drive, Tri-State view, and everything else similar to Sears Tower.

While Sears is special in its own way for being on a ledge 1353 ft above the ground hanging in the air known as Skydeck outside the tallest building above Chicago River, Hancock offers a 360° view with an incline feature called Tilt plus no long lines. The cherry on Top, Signature Lounge coffee, and the highest indoor pool.

But if you wanna visit any of these skyscrapers at the night, Sears alias Willis Tower is the best option for its electrifying view of Chicago streets. Sears Tower also planning to host a spine-tingling slide from its 103rd floor to 102 outside the building which might turn the odds completely.

Nightview from Sears Tower
Night View from Sears Tower Chicago

Magnificent Mile:

Walk the famous mile of Chicago with the top-class brands for some window shopping. The holiday season is the most famous time to walk this mile with thousands of people around and spectacular decorations. Especially, Magnificent Mile Lights Festival cannot be missed during this season.

Grab famous Girardelli ice cream just immediately after descending the John Hancock Center and start enjoying the walk a mile. While you are halfway there, you are probably on one of the most famous double-deck bascules Chicago-styled bridges – Michigan Avenue Bridge surrounded by super skyscrapers – The Hyatt, The Trump Tower, and The Wrigley building.

Enjoy the view and breeze from Michigan if you are lucky the wind isn’t chill-killing. Hop on-Hop off bus tours provides all we need or walk to the lower level of the bridge for an Architecture tour on the Chicago River for 75 minutes and learn all about Chicago. Also, Riverwalk all along offers not-to-miss local beer with many more amazing moments. Talk to lovely local people who jog all the trail from Wacker Dr to Navy Pier and all the way to Museum Campus.

The Bean:

End of the mag mile is Chicago’s famous architecture wonder, Cloud Gate aka The Bean. One visit is not complete without checking in here. Known for its classic sculpture style which shows Chicago’s skyline on its body. Don’t forget to swoop in to experience the ‘navel’ beauty of the sculpture.

While you are here, you might not wanna miss “the authentic” thick crust Giordano’s pizza, because why not. But the local favorite pizza is Lou Malnati’s which is much more delicious and we personally love it.

Soldier Field and Navy Pier: 

10 min drive from The Bean or the preferred 15 min bike ride – Divvy – Chicago’s Bike Share System along the lake trail, you will land into the most happening place – The Museum Campus. Buckingham Fountain would have cheered you up halfway thru the drive.

Buckingham Fountain Chicago
Buckingham Fountain

One can spend more than a day at the Museum Campus with The Shedd Aquarium that has spectacular shows and animal species, The Alder Planetarium first of its kind in The United States, The Field Museum – one of the largest natural history museums and the home field of Chicago bears – Soldier Field. All you can see with all the time one has.

If you are planning to visit at least 5 of these attractions in 9 consecutive days, Chicago CityPASS might help.

Walk down the steps at the end of the Solidarity drive to experience the stunning Skyline view of Chicago. One can see all skyscrapers from the far left with the black tall standing poles of the Willis Tower to the rightmost black skyscraper The Hancock Tower and across the lake, is the Navy Pier.

Take a 10 min ferry ride from Shoreline Water Taxi located on Lakefront Trail to Navy Pier and experience Chicago’s ferry wheel, have some leisure time with a local beer on one of the benches enjoying the infinite view of Lake Michigan, or take a thrilling ride in Lake Michigan and party hard in one of the many docked Ships.

Chicago skyline view
Skyline View from The Adler Planetarium

The Museums:

Chicago has a lot of history to learn and lucky we, the top-notch museums in Chicago stored it all. The Field Museum is the best of all and one can spend here days appreciating all its exhibits from Egypt to Native America. Art Institute of Chicago’s Contemporary exhibition, Science Storms in Museum of Science and Industry, Mexican Art in Museum of Mexican History, never-ending cultural and sports museums are just a few of thousands of exhibits among Chicago’s most popular ones. Museum of Illusions is our latest favorite.

Field Museum
Exhibit in The Field Museum


Lincoln Park zoo, just outside the downtown is a quickie plus it’s free. While you are here, don’t miss out on North Avenue Beach which offers a splendid view of the Chicago skyline.

If you wanna see more species and can spend a complete day, Brookfield zoo is the right one. An hour ride from Chicago’s most beautiful Central rail station – Union station in downtown has convenient Metra trains. Jumbo Pandas, Cuty Teeny Penguins, Dolly Dolphins.. did you hop on to train already?


Rock n roll in Chicago never ends. With plenty of clubs, bars, and theatres, it offers all types of entertainment after a busy day. One can never miss operas in Civic Opera House, classic old shows in Chicago Theatre on State street.

Late-night hangouts? Chicago’s Grand Street has it all. One can visit – Soundbar for best EDM now while karaoke lovers have House of Blues just under Chicago’s famous and first apartment complex – Marina Towers. Guess the James Bond movie shot here.

Fado’s Irish pub is not to miss on game days. Late-night? The Detention is pretty nightclubs in Chicago downtown but if one can go an extra mile or I should say to an extra state, an hour n a half drive from Downtown, The Atlantis is all one looking for. Worth the drive. Period.


Chicago sports clubs have their own style and fans go crazy on game days. Bulls, Blackhawks, Bears, Cubs, Whitesox, and so on for every game out there. The Blackhawks match in United Center, Wrigleys for Cubs, and the Bears in Soldier Field are absolutely stunning. Soccer fans sometimes get lucky in Soldier Field.


Champion of restaurants – Chicago’s best Alinea is here. Unique experience and of course $$$$$. Craving for the best shrimp in town? Mccormick’s and Schmicks is the one you looking for. Looking for an upscale bar? Sweet water it is. Girl and Goat for some signature dishes. Bub City for barbecue. Authentic P.F. Chang’s on Wabash Avenue is another top beat.

P.F.Chang’s in Downtown Chicago
P.F.Chang’s in The Downtown

Indian in Downtown? Jaipur restaurant for yummy lamb biryani. No buffet, please. But for authentic Hyderabadi Biryani with Haleem, more like street food, the smaller Hyderabad House on Devon street with the blue board is the one you looking for. Yes, they are two just across the road. Remember to carry cash and avoid parking but take out. Masala in Naperville has a famous Indian buffet. Bombay Chopsticks in Schaumburg is the most authentic Indo-Chinese restaurant one must try. Both these latter spots are an hour’s drive from Downtown.

For more unique restaurants Downtown, check out Moti, RAMEN-SAN, Doughnut Vault, hot dog and Chocolate Cake or Shake at Portillo’s, best ice cream flavors at Jeni’s, pudding at Magnolia Bakery, and Donut icecream at Firecakes Donuts. There are so many more and my full list of saved restaurants can be found here.

Of all, street style is always best. Nothing beats Al’s Italian Beef, hot dog at Hot-Doug, Yum-Dum for dumplings. Garrett popcorn and Cheesecake Factory to end a meal. And of course, list never ends.


North of Downtown is pretty with lots of awesome beaches  – Glencoe, Grosse, Montrose, and North Avenue beach. Also The Baha’i, the most beautiful House of Worship and the one and only in the United States is located in Evanston, 30 min from Downtown. Chicago Botanic gardens for its famous Japanese style is one-time visit. Six Flags Great America is further north, an hour’s drive.

Northwest is Schaumburg for many Indian restaurants. West is Naperville with a famous Indian temple – Aurora and Chicago outlets for budget shopping. The Morton Arboretum, a large public park with thousands of trees for fresh air is also around and if visiting in the Holiday season, lights show is a must.

There are so many beautiful events to catch up on during the holiday season from the Let It Shine show in Northbrook, Christkindlmarket, Christmas Tree at Millennium Park, Macy’s holiday displays on State street, skating at Millennium Park, and so on. Check out full list of things to do at

Bahai Temple Chicago
Baha’i House of Worship

That goes without saying, Chicago has a lot to offer and this is just a beginning. Shameless on Netflix remind me Chicago everytime. Enjoy your visit to Chicago and explore the town like a local now.

Keep having a good day (Chicago’s South Side Style).

Still, need a reason to visit Chicago? Hope these inspire.

Cheers and Safe Travels!

About Author

“Be a Roman when in Rome” is the first travel quote I heard. Soon I realize every place is unique. Wondering how it is? Well that's why the stories here are for. Enjoy reading them!

With so many lovely places on this earth, different cultures and variety of food, exploring one at a time while leading a crazy IT professional life. In short, call me Explorer, be it places, food or IT. See you around!

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