Samarth's Guide to Chicago

May 06, 2023

As a resident of Chicago, the greater Chicagoland area (for the majority of my life), the Bay Area, and (somewhat more dubiously) New York City, and having traveled to all ends of the United States, I can say, with confidence, that Chicago is the best city in America, and potentially the world.

Now, before you contest my statement, let’s clarify what “best” means in this context. I’m taking into account nightlife, daytime activities, and overall quality of life. While New York might boast superior nightlife, Chicago offers a better quality of life before 10 pm. San Francisco may have a closer connection to nature, but it pales in comparison to Chicago’s vibrant nightlife. In essence, Chicago is the metropolis that most effectively balances these crucial aspects of urban living.

Planning a visit to Chicago can feel daunting, with so many sights and activities to choose from. Fortunately, when you search for “things to do in Chicago,” you’ll discover that the city’s iconic attractions are genuinely exceptional. Unlike some cities (ahem, Times Square), Chicago’s tourist hotspots are must-sees that won’t leave you disappointed (looking at you, Union Square).

In this blog post, I’ve compiled my top recommendations for places to visit in Chicago, as well as some fantastic dining options. Hopefully this guide can help add some direction to your trip, and help you fall in love with Chicago just as much as I have.

If you have any ideas or suggestions on additions to this guide, feel free to email me at

Recommendations and hitlist in spreadsheet form: Samarth’s Guide to Chicago

Update: A quote of mine was recently featured in an Apartment Hunt article! Check it out here.

Places to Visit

Must See Destinations

  • Navy Pier
  • Willis Tower
  • Millenium Park
  • Magnificent Mile
  • Chiago Riverwalk
  • Grant Park and Buckingham Fountain

Experiences and Visits

Must-Do and Must-See

  • Chicago Architecture Boat Tour
  • Northwestern University and Evanston
  • Bike along Lake Michigan
  • Any of the Beaches!


  • The Field Museum
  • The Shedd Aquarium
  • The Adler Planetarium
  • The Museum of Science and Industry
  • The Art Institute of Chicago

Additional Recommended Experiences

  • Chicago’s Chinatown
  • Lincoln Park and Lincoln Park Zoo
  • Evanston Bahai Temple
  • Fulton Market
  • Free Concerts in Millenium Park
  • Brookfield Zoo
  • University of Chicago

Places to Eat

Price: $

  • Firecakes Donuts
  • Nutella Cafe
  • Culvers
  • Nando’s PERi-PERi

Price: $$

  • Lou Malnatis Deep Dish Pizza
  • Pequods Deep Dish Pizza
  • Velvet Taco
  • Lao Sze Chuan
  • Au Cheval
  • QXY dumplings
  • Sumu Ramen

Price: $$$

  • Girl and the Goat
  • Proxi
  • Galit
  • ROOH
  • NoMI
  • Trivoli Tavern
  • The Purple Pig

Price: $$$$

  • Boka

My Hitlist

Having spent the majority of my life in Chicago and the surrounding areas, I’ve curated a somewhat selective list that emphasizes lesser-known, unique attractions that don’t garner the same attention as the more prominent destinations mentioned earlier. A word of advice: don’t regard these experiences as hidden gems just yet. I recommend immersing yourself in the quintessential Chicago attractions listed above first, to fully appreciate the city’s essence, and then consider exploring these additional experiences for a more comprehensive perspective.


  • Color Factory Chicago
  • The WNDR Museum
  • Garfield Park Conservatory
  • Frank Loyd Wright House


Price: $

  • Publican Quality Bread

Price: $$

  • High Five Ramen
  • Green Street Smoked Meats
  • HaiSous

Price: $$$

  • Momotaro
  • Monteverde
  • Parachute
  • avec

Price: $$$$

  • Claudia
  • Smyth
  • Ever
  • Oriole
  • Alinea


Shoutout to my parents for deciding to settle down in the Chicago suburbs and for letting me explore as a kid. I always loved visiting the big city, and am eternally grateful for the opportunity to be able to see the world around me as I have and hope to continue doing.

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Written by Samarth, a builder, problem-solver, and amateur gymnast.