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Our home away from home, Chicago is an extremely underrated city with a fantastic waterfront, architectural jewels, a vibrant urban life, and years of cult history. Arguably the best city in the American mid-west, the Windy City, hosts a number of museums, art galleries, and hundreds of famous restaurants and bars. The cost of living is much lower than the two coasts yet residents enjoy all the privileges of an ultra modern metropolis.

Being our hometown for a while, the writing is going to be slightly biased and long, but we will try to point out the highlights without stretching the patience of the readers.


The first thing that you will notice once you are in the city, is that the city is broken down into a bunch of neighborhoods, commonly known as the hoods. Anyone living out of the city, lives in burbs, i.e. suburbs. The central part of the city with the financial district and

downtown is called the Loop (named after the metro rail “L” line that circles around the center of the city). Outside the loop, there are various types of neighborhoods, upscale River North and Streeterville, artsy Gold Coast, classy Lincoln Park, hipster Wicker Park and Bucktown, slightly sketchy(!) South Loop, and meat packing district of West Loop. All the hoods have their own vibe and culture, and are filled with small businesses and local restaurants.

There are other hoods that are dominated by specific races and nationalities like Chinatown, Greek Village, Russian Village, Ukrainian Village, Little Italy, etc. As the names suggest, you will find authentic food and culture hidden in these little neighborhoods.

Touristy Attractions

Depending on when you visit Chicago, there are different things to do. For the most part, summer (May-Sept) is definitely the best time to visit the city with a plethora of events and activities that attract tourists and participants from around the world. We will cover a high level list of events later. But first, lets dive in on the attractions. For a one day itinerary, follow the order below –

  1. Millennium Park – Located right on the banks of the Lake Michigan, Millennium img_4357park hosts a number of stunning architecture, sculpture and landscape designs. The famous Cloud Gate is the star of the show with its curvy shiny surface molding the city-scape and humanoid figures within its reflective surface. Best time to see this marvel is in the early morning right after sunrise. There will be a crowd anytime after.
  2. Art Institute – Across the street from Millennium Park, is the famous Art Institute of Chicago. While you walk south along Michigan Avenue, you will encounter a number of sculptures by local artists, a park and garden, and the img_5309fountain of peace. The Art Institute houses some of the extraordinary pieces of artwork from surrealism, impressionism and renaissance age to modern cubism. Masterpieces include Manet, Monet, Dali, Matisse, Picasso, Van Gogh, Degas, and many more. This was also the place where the great Indian Monk Swami Vivekananda gave his eternal speech at the World Religious Forum in late 19th century.
  3. Park System – After exiting the Art Institute, walk south along Columbus avenue (one block east of Michigan Ave), and cross the bridge to enter

    Maggie Daley Park. This is part of the Chicago Lakefront Park system that stretches from the south loop to Montrose harbor in the north along the lake front. In the park, there are gardens, rock climbing, mini golf, sculptures, statues and fountains atop a massive green space. The walkway provides an unparalleled view of the Chicago skyline. Towards the south of the park is the Grant Park with the Buckingham Fountain, which are worthy of a photoshoot, be it in the day or after dark. Spectacular view of the south loop along with the historic Congress Hotel can also be cherished from the fountain.

  4. Lakefront – From Grant Park, cross the street into the dock on the lake for a lazy

    stroll in either direction. If you are in the mood to walk for 30 minutes or so, you can walk north towards Navy Pier. On summer Wednesdays, there is a spectacular fireworks show at Navy Pier that starts around 9PM. In general there is nothing to do in Navy Pier, apart from great views and a quick lake cruise.

  5. Magnificent Mile – If you have time in the afternoon/evening, walk along Michigan avenue from the river bridge (DuSable Bridge) up north. This is the shopping district with most of the major upscale brands (comparable to 5th Ave in NYC). Best activities here are people watching, shopping, and fine dining.
  6. Architecture Tour and Riverwalk – In summer, it is a must do for a Chicago visitor. Walk along the riverfront on the south side of the river from Michigan ave to the lake. From the river front southeast corner of Michigan ave., the boat departs (Check schedules) for an informative tour along the river upstream and then back to the lake. On the way, you will see and learn about the famous Chicago architectural landmarks, e.g. Aqua, Aon Center, Carbide and carbon building, Manhattan Building, Willis tower, Marina City, Hancock tower, Merchandise Mart, Tribune Tower, Trump Tower and Wrigley Building.
  7. Museums – While there are a plethora of museums in the city, the crown jewel is the three-museum campus with Adler Planetarium, Shedd Aquarium, and the Field Museum. Budget for a full day to visit all three in the south side of the loop (south loop). Even if you have been to the other Natural History museums, the Field museum is special not only because of the 40′ tall T-Rex Sue skeleton, but also for the extremely informative galleries. As an added bonus, you get a fantastic view of the city from the south. TIP – Take the water taxi from the museum campus dock to Navy pier. It is a journey worth doing to admire the Chicago skyline from the lake.
  8. Other attractions – Going up to the Willis Tower Skydeck (the Ledge), a drink at the top of the 95th floor in the Hancock Building, Macy’s on State Street, Water Tower, Chinatown, Chicago Theater, etc. are some of the things you can do if you have the time.
  9. Gastronomic Adventures – But if you have time, we suggest diving into some of the fascinating food options the city has to offer. Known as the meat packer of the world, the city is indeed a food lover’s paradise. Here are a few of our favorites –
    1. Breakfast and Brunch: Rick Bayless’ Xoco, Bongo Room, The Whisk, Stan’s Donuts, coffee at Intelligentia Coffee
    2. Lunch: Grab a nice Deep Dish Pizza at Pizzeria Uno or Giordanos.
    3. Dinner: Fusion food in Avec or Vermillion. Peruvian food at Tanta, Spanish tapas in Cafe Babbareeba, Burger at Au Cheval, american fare at The Publican, or food comprised only of a hog at The Purple Pig.
    4. Nightlife – Chicago has many options for a night time escapade, but Hubbard Street has several pubs and clubs for a late night out. Some of our favorites are Howl at the Moon, Paris Club, and Three dots and a dash.

Seasonal Activities

Chicago has a bunch of activities that run year round. But some of the key ones that we loved are –

  1. Taste of Chicago – In a weekend in July, all the eateries in Chi town come together in a weekend long fair to taste the various delicacies of Chicago. The famous Polish Dogs, Chicago Hotdogs, Pizza, Hamburgers and Donuts can all be tasted at the same venue in Grant Park next to the lake.
  2. Chicago Auto Show – In the frigid cold of January/February, the autoshow comes to town. In the massive arena of Mckormick Place, the famous brands of cars are on display. We met some of our dream cars and a couple of ‘next’ cars in this show that we are proud to drive now.
  3. Lolapalooza – This can be the festival of the teenagers, but young and adults equally have fun in this fun filled musical event in July. Also hosted by the lake, the city comes to a standstill during the Friday and Saturday of the famed festival, Lola.
  4. Chicago Marathon – Come October, the city welcomes thousands of participants toimg_6146 the Chicago Marathon. Hotel rooms get sold out and traffic comes to stand still on the Sunday morning of the Marathon event.
  5. Blues and Jazz – The world’s largest free Blues festival happens in Grant Park in June. Also, the city is famed for Jazz which can be enjoyed at numerous Jazz clubs in the loop and other hoods.
  6. Pride – In June, during the national pride month, the Lakeview neighborhood (just north of Lincoln Park) gets to celebrate the Pride parade and shows. It is a festivity that you cannot miss if you happen to be in town during that time.
  7. Air and Water Show – In August, watch the famed Blue Angels and other display some tricks in the sky with the expansive lake in the background. Navy and Airforce comes together in this frantic display of planes and ships.
  8. America’s Cup – In some of the years, the America’s cup sailing world series comes to Chicago with the top sailors testing the fierce waters of the lake Michigan in August.
  9. Cubs Game – Root for the ‘lovable losers’ (NOT ANYMORE), err World Series img_4318Champs’16  Chicago Cubs in Wrigley Field. Do Not Attempt to go to a White Sox Game though. Kidding (I am a Cubs fan).
  10. St. Patrick’s Day – With the parade on Columbus drive, the river dyed Green, and festivities all around, do not miss out on drinking some green beer in one of the Irish pubs downtown on St. Patrick’s day in March.

That’s all for now. We will add more posts and pages if needed. But believe us, Chicago has way more things to do and enjoy, especially if you are a foodie, art lover or a casual city guy.

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