Destination highlight and Itinerary: 48 hours in Chicago

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Trupti Devdas Nayak

Traveler . Writer . Photographer . Artist . I write about outdoor adventures at and my travels at
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The best time to go to Chicago is NOW!

Wondering where to go this summer? Looking for the perfect weekend getaway but not sure where? I have one word for you: Chi-caaa-go!

Why, you ask? Oh, do I have a surprise for you! Chicago knocked my socks off and I’m sure you will be blown away too; literally since it’s known as Windy City and figuratively because it’s incredibly versatile and diverse with the types of experiences it offers travelers.

What are some of the things you would imagine a perfect destination should offer?

Here we go with our pop quiz!

  1. World Famous Landmark? Check
  2. Art? Check
  3. Architecture? Check
  4. River Cruise? Check
  5. Comedy and Improv? Check
  6. Rich history? Check
  7. Top-notch Michelin star restaurants and gourmet dining? Check
  8. Live music? Check
  9. Speakeasies? Check
  10.  Nature fix? Check
  11.  Sandy beaches? Check
  12.  Birds-eye views? Check
  13.  Opulence? Check
  14.  Rooftop bars? Check
  15.  Shopping? Check
  16.  Movie magic? Check
  17.  Family friendly? Check

No surprises there, Chicago checks them all!

A world famous landmark

Chicago boasts the “Bean”, a spectacular work of art housed in the center of the city amidst verdant Millennium Park. Resembling a silvery drop of mercury frozen in its volatility, the Bean radiates modern aesthetics with its smooth curved surface, offering an introspective glimpse through its dynamic reflections of surrounding skyscrapers and visitors. 

ProTip #1: Go early in the morning or late in the evening to avoid crowds.

ProTip #2: Don’t forget to look up when walking underneath the Bean. The kaleidoscopic funhouse-style reflections are incredible!

World famous Art

Did you know that one of the world’s best museums, the Art Institute, is in Chicago? Housing some of the best works of Van Gogh, Seurat, Monet, Manet, Picasso, Rembrandt, Thorne’s miniature rooms, Greek sculptures, ancient statues of gods and goddesses from India and Asia and more, the Art Institute is the perfect place for art aficionados and amateurs alike. Plan to spend a full day at the museum (open from 10:30am – 5pm), the outdoor café in the courtyard overlooking the water is a great choice to take a break for lunch. If you’re not into magnets, a mug printed with an impressionist painting (how about Van Gogh’s bedroom?) from the museum makes a great souvenir.

ProTip #1: Make sure you go on one of the free docent-led tours at the Museum, inquire about timings at the information desk. We learnt more about all the art and life of the artist’s of those eras when spending 45 mins with an enthusiastic and knowledgeable docent than we did listening to the audio tour narration when exploring the museum on our own.


Chicago invented skyscrapers, duh! It’s no surprise that several of the Batman movies featuring the brooding skyline of Gotham City were shot in Chicago. There are dedicated river cruises like the highly rated and recommended Chicago Foundation Architecture River Cruise that take you down the Chicago river on a leisurely 1.5 hour cruise, where you can soak up the history of the glorious buildings towering over you as an enthusiastic guide explains the stories behind each building. Soaking in some sunshine with a summer shandy in hand when cruising the river on the Lady was perhaps one of my most memorable river cruises ever. And the cherry on top? When the boat makes it’s way out of the mouth of the river to Lake Michigan and you get a panoramic view of the Chicago’s entire skyline. Breathtaking.

ProTip #1: Buy your tickets for CFA online so that you can choose the day and time of sailing in advance. Plan to be at the boat dock 30 mins prior to boarding.

ProTip #2: Be the first in line to board! The best seats on the boat are the last row on the left (row with two seats). There are several advantages to sitting at the back, you can stand up whenever you like to get a better view without obstructing anybody else. If you’re sitting in the rows that have 2 seats, you’re able to get in and out easily to access the bar or bathroom. Most of the buildings that the docent spoke about were on the left of the boat, but the right is fine too. You’ll be craning your neck up to take in the towering skyscrapers as you cruise along the river anyway, so it doesn’t matter which side you sit on.

Comedy and Improv

Are you a fan of SNL (Saturday Night Live) and love watching all of these incredibly talented and creative people like Stephen Colbert, Tina Fey, Amy Poehler, Seth Meyers and Vince Vaughn? Then you’ve come to the city where these people trained and learnt their skills and honed their talent, getting ready to entertain millions of people around the world. Chicago is the home of Second City, world-famous for Improv classes, workshops and shows. There are several iconic institutions to choose from for watching a show, whether you want to see Improv, Standup Comedy or more. In addition to Second City, there’s Improv Olympics (IO), and Chicago Improv.

ProTip #1: Book the tickets for the days and shows you want to see in advance, these are often sold out weeks in advance.


Chicago was incorporated as a city in 1837. As a bustling trading center, Chicago played a leading role in the country’s expansion. Even the Great Chicago Fire of 1871 could not dampen this city’s indomitable spirit. Everywhere you go in Chicago, the buildings, streets and underground structures showcase the ingenuity of its residents. Chicago is also the birthplace of the country’s first skyscraper which was built in 1884. That building may no longer exist since it was demolished, but today, the Sears Tower (standing at 1450 foot) continues to hold the title as one of the tallest  buildings in the country and the world. 

Top-notch restaurants and gourmet dining

Chi-town is home to some of the best restaurants in the country and even the world. Remember Bravo’s Top Chef? The first female winner Stephanie Izard founded one of Chicago’s most popular and famous restaurants named “Girl and the Goat”, which is a must to dine at, especially if you love goat/lamb. Some must-try dishes include the Brioche Bread served with chive butter and lamby jam, the roasted broccoli with goat cheese, the empanadas stuffed with goat and the wood fired lamb ribs. We were so stuffed, we didn’t have any room left for dessert. Every dish tasted exceptional and the service was friendly and on point.

ProTip #1: Make reservations well in advance as Fridays and Saturdays fill up quickly. When looking for reservations a day earlier, I got lucky and scored a 7pm reservation on OpenTable for Sun evening. Later, while waiting to be seated, we overhead walk-ins being informed that the wait would be 1.5 hours without reservations.

ProTip #2: Portions say “small plates to share” but are pretty generous. Unless you’re starving or really craving meat, getting 3-4 plates should suffice for two.

Live music

Chicago is the birthplace of the blues and jazz! There are several amazing places to choose from, the ones recommended to us which we loved checking out were Kingston Mines (blues) and The Green Mill (jazz). We adore live music and have been to New Orleans and Austin (two other amazing cities for blues and jazz). Kingston Mines in Chicago felt raw and authentic and the several hours we spent there went by in a happy blur. We went to Green Mill pretty late on Sunday night, so the crowds were gone, but the jazz trio was gearing up to play till 4am!

ProTip #1: Sit or stand as close to the stage as possible. Watching the singers and guitarists and drummers up-close is immersive and the best way to experience the raw power of music.

ProTip #2: Kingston Mines has 2 stages. The smaller stage had a band playing during dinner, and the larger stage was setup to play at 10:30am. They keep playing till 4am! You can order food at Kingston Mines if hungry, the onion rings are delicious as are the po’boys! Note that Green Mill does not offer food, but there are places next door that do.


Having experienced several speakeasies around the country (San Francisco, New Orleans, Austin), I must say that my experience at the Office in Chicago was by far one of the most memorable. Touted as one of the most notorious speakeasies to get into, the Office came highly recommended by a friend who visits the city often. I hadn’t made reservations in advance, but when I checked on their website a couple days before the weekend, Fri and Sat were already booked up and they had limited availability for two time slots on Sunday – 8pm and 10pm. Read my post about about our unique experience and what makes the Office a must-visit in Chicago!

ProTip #1: Ask for Christiana at the Office. She is as spirited as the spirits she blends into delicious cocktails and she astounded us with her knowledge of everything related to alcohol, spirits, the Prohibition and more, while delighting us with her custom-made drinks.

ProTip #2: If you’re feeling peckish for dessert, get the icecream sundae which comes with a side of hot fudge/caramel sauce and an entire tray of toppings to choose from, making you feel like a kid in a candy shop.


Even in the heart of the city, surrounded by skyscrapers, you can escape the urbanity of it all in Millennium Park (the home of Chicago’s world-famous Bean at Cloud Gate). Lush green landscapes, walking paths, bike-friendly trails, the Jay Pritzker pavilion (outdoor amphitheater) and Zumba in the park (on weekends).

Sandy beaches

If this is your first visit to Chicago, you will be stunned to see sun-bathing people on a beautiful sandy stretch of the beach on the shores of Lake Michigan. Right near downtown with a view of the skyscrapers and easily accessible by bike paths, Oak Street Beach (among many others) is definitely worth a stroll even if you don’t have time to don a swimsuit and jump into the refreshingly cool waters of Lake Michigan on a hot summer day.

Birds eye views

Not just one, but two incredible options to choose from! If you’re not afraid of heights, do both! The Sears-Willis tower with the glass “ledge” is one of the most popular spots in Chicago to take in the city views. Another strong contender is the 360 degree Observation Tower (previously known as John Hancock tower) with its “sky-dive-vertigo-inducing” TILT experience. If the weather is good, go to both!

ProTip #1: Buy the “Sun and the Stars” ticket for 360 degree Observation tower which allows 2 visits within 48 hours, so you can go during the day time and then visit again at night for the twinkling city lights.

ProTip #2: If you want to visit just once, go an hour before sunset, so that you can admire the golden glow of the setting sun being reflected off the buildings and hang around for an hour after sunset to see the city lights come on one by one.


If you’re feeling like royalty and want to soak in some decadence, look no further than afternoon tea at the Drake Hotel. The historic hotel was built in 1920 and the “high tea” offered at the Palm Court restaurant is legendary. Reservations recommended in advance. I got lucky again with looking for availability on OpenTable a couple days before, and finding a 1:30pm time slot available for 2 people for Sunday! Afternoon tea is not an experience to be rushed, so expect to spend 1.5 – 2 hours at leisure.

ProTip #1: Request your host to seat you as close to the live harpist as possible. Listening to her play Edelweiss, Fur Elise, the Godfather tune and other quintessential classical pieces was a delight as we sipped on our teas and ate our sandwiches.

ProTip #2: Get the fruit tea or tropical tea, refreshingly different from the green/black teas, these are made with real fruit pieces like mango, papaya, pineapple and is truly smells and tastes like bouquet of fresh fruits in a cup.

Rooftop bars

It’s no wonder that with its proliferation of skyscrapers, Chicago offers an astounding array of rooftop bars where you can sip on a Bloody Mary when taking in a bloody spectacular view. Cindy’s was recommended to us by several friends and totally exceeded our expectations. This is one of the few rooftop bars overlooking the Millennium Park with a view of the Bean.

ProTip #1: Dinner reservations are required in advance, else seating is first come first serve at the bar.

ProTip #2: There might be a wait to ride the elevator to the top, so once you get to the 13th floor, make a beeline to the outdoor balcony which will invariably be full of people jostling for a spot to take in the views. Wait for a few mins patiently and somebody is bound to make space for you to take a peek over the railing. The views are worth it!


If browsing stores and shopping for top brands is your perfect vacation (it’s called retail therapy after all), look no further than the Magnificent Mile or the “Mag Mile”. Lined on either side with world-class brands like Louis Vuitton, Chanel and Burberry, you can spend an entire day just popping in and out of these stores and lugging along glossy paper bags filled with all the beautiful things your heart desires.

Movie Buffs

I mentioned Gotham City and Batman in passing under “Architecture” and there’s a lot in Chicago for movie buffs. Some of the Hollywood movies that have been shot around here are Divergent, Transformers, Superman, Ocean’s Twelve, Spiderman and more. In fact, there’s even a movie-themed tour visitors can take to experience a slice of Hollywood magic.

Family Friendly

There are tons of activities and places to see and do when visiting with the family. The sandy shores of Lake Michigan are perfect for a day of swimming and lazing, the Shedd aquarium is bound to keep kids enthralled with the magnificent creatures of the sea, Millennium Park and the outdoor art exhibits with water fountains are the perfect excuse to cool off on a hot sunny day and the river cruise is a fun experience for the young and young at heart. The Art Institute of Chicago is a hit with older kids who are interested in learning more about the world’s famous artists from Van Gogh and Monet to the painstakingly created Miniature Thorne rooms.

Now if all of the above has convinced you that you need to plan a visit to Chicago this summer, here is some additional information on travel logistics!

What about accommodations?

Airbnb! We stayed at an adorable Airbnb in Logan Square, a residential neighborhood with wide boulevards and incredible breakfast/brunch places within walking distance like Bang Bang Coffee and Pie. Logan Square boasts wide boulevards lined with leafy trees, friendly neighbors walking dogs, brick buildings (something we don’t get to see in earthquake-prone California often) and is located a short Lyft ride away from the city’s main sights. Our amazing hostess Arryn (Justyne’s roommate) welcomed us into her home and we felt like we were staying at a friend’s place in the city. Although we didn’t meet Justyne in person since she was out of town, staying in her room made us feel like we got to know her just by browsing her many accolades (an interview with her was published in the Chicago Tribune!) and accomplishments (she’s a certified bartender and a graduate of Second City improv) and thoughtful touches (pillows cheerfully declaring “good morning sunshine” and “love”) around the room. Thank you Justyne and Arryn for a wonderfully warm stay in Chicago!

How do I get around Chicago?

If you’re there just for the weekend and don’t want to bother with renting a car and figuring out parking in downtown or near landmarks etc, just use Lyft to get around. Lyft Line (carpool) is even cheaper and we were able to get around most of the city sights for $4 – $7 per ride.

Also, many of the sights on this list are within walking distance from each other. For example, Cindy’s with the spectacular rooftop views of the Bean and Millennium Park is a 2 block stroll from the Art Institute of Chicago.

What about the weather?

Just from my experience of spending a weekend in Chicago, all I can advise is, the weather predictions can be completely incorrect given the influence of nearby Lake Michigan. The weekend we were visiting was supposed to be rainy with thunderstorms and lightning. Since our travel dates were not flexible, I was determined to enjoy Chicago, thunderstorms and all. I packed my umbrella and rain jacket and even a rain cover for my backpack. Funnily, the forecast kept changing every few hours! Grabbing the opportunity, we booked our Chicago Architecture River Cruise for the next morning when it was supposed to be partly cloudy (and hopefully no rain). Saturday dawned bright and full of sunshine! We had a wonderful river cruise and were happy to get one brilliant day in Chicago. Bring on the rain, we thought. But no, the weather gods had other plans – thank you! Overnight, Sunday’s forecast changed to partly sunny! It was a pleasant 70 degrees the next day when we were inside the Art Institute and we got clear blue-sky views of the Bean, millennium park and the city skyline in the evening from Cindy’s rooftop bar. In the forecaster’s defense, there were a few drops of rain that fell on my head on Saturday evening. So atleast the forecast was not entirely incorrect! Long story short: Plan for whatever weather you may get, and make the best of it.

Additional Tips and Recommendations:

Thanks to friends who’ve lived in Chicago, here are additional places to check out and things to do if you have time.

  1. Randolph Street Restaurants
  2. Navy Pier
  3. Lincoln Park
  4. Old Town
  5. Howl at the Moon – fun piano bar in downtown
  6. The Violet Hour – recommended speakeasy, no reservations, first come first serve
  7. Shedd Aquarium
  8. Sundo – sushi / asian fusion restaurant
  9. Au Cheval – best burgers in town!
  10.  Portillos – great hot dogs
  11.  3 arts café club – brunch! Does not take reservations, so be prepared for a line

And here’s a proposed itinerary to help plan your perfect weekend getaway in Chicago! Note: The following is what we did in 48 hours in Chicago. You should spread out the itinerary if spending more than just the weekend in the city.


   Arrive in the evening and check into your Airbnb

   If flying from the West Coast, you lose 2 hours, so even if you fly out in the evening, you’ll reach pretty late at night which means you won’t have time to see much that night

   If flying from the East Coast, you’ll gain an hour, so might as well head out after checking into your hotel / Airbnb, and grab dinner at one of the places mentioned above, and head over to Kingston Mines for Blues or Green Mill for Jazz (both open till 4am!)


   Light breakfast near the hotel / Airbnb (save your appetite for high tea!)

   Get to the dock in time for the Chicago Foundation Architecture river cruise and check-in

   11am – 12:30pm River Cruise

   Walk 10 mins to the Drake Hotel

   1:30pm Afternoon Tea at the Drake Hotel (allow 1.5 – 2 hours)

   Walk 20-30 mins to Second City. This is a great excuse to digest all that food and also  you get to walk along the sandy beachy shores of Lake Michigan and watch as families, friends and couples sunbathe and swim in the blue waters

   Get to Second City, check-in for the 4pm show, grab a seat and order a drink. Enjoy some real good laughs from talented comedians!

   The show ends by 6pm, so walk over to 360 degree Observation deck and ride the elevator to the top. You can enter with pre-booked admission and get to the observation deck to watch the sunset. If there’s no long line for the “TILT” experience, go for your turn at experiencing dizzying heights!

   After you’ve watched the city lights twinkle on and spent a couple hours at 360 degree observation deck, take a Lyft from Second City to Kingston Mines

   Order some onion rings and po’boys for a late dinner while enjoying the live music blues

   Move to the main stage for the 10:30pm band

   Dance away any blues while listening to the blues!


   Breakfast at Bang Bang Pie and Coffee for incredible biscuits and the best pies in town

   Take a Lyft to Art Institute of Chicago, plan to arrive by 10:30am right as they open

   Buy your admission tickets and grab a copy of the map and audio tour

   Head straight to the Impressionism exhibit and make your way taking in the world-class paintings

   Head back to the lobby for the 12pm free docent-led tour (45 mins duration)

   After the tour, pick up from where you left off and make your way around the museum

   Avoid the noon lunch crowd by going late after 2pm to one of the museum cafés for a bite

   Make sure you don’t miss Thorne’s Miniature Rooms (incredible attention to detail and life-like) If you ever dreamed of feeling like Gulliver towering over tiny houses, this is the place for you!

   If you’re a fan of handmade glass paperweights, you’re in luck! There’s an entire room dedicated to these precious unique beautiful glass creations!

   ProTip #1: Midway through your day, drop in at the gift shop to browse through and make sure you haven’t missed any of the must-see exhibits in the museum. The gift shop postcards and souvenirs always display the highlights of any museum and are a great place to take stock of what you’ve seen so far and make note of what’s remaining to be seen

   ProTip #2: For the Thorne Miniature rooms, go later in the afternoon (after 3pm or 4pm) to avoid the crowds, since they are especially popular with kids in the mornings

   When the Art Institute closes at 5:30pm, make your way out (don’t forget to take a photo with the imposing bronze statues of the roaring lions outside the museum) and walk 2 blocks to Cindy’s rooftop bar

   There might be a line to get into the elevator that whisks you to the 13th floor, be patient as the line moves quickly. Take note of the floor tiles and wonder why they look like the bottom of a swimming pool!

   When you get to the top at Cindy’s make a beeline to the outdoor balcony and take in the views. If you have time, get a drink at the bar, but we eschewed this in favor of just enjoying the views, especially since there was a long line to order a drink

   When you’ve had your fill of the views, take the elevator back down and grab a Lyft to go to Girl and the Goat restaurant for your 7pm dinner reservation

   Allow at least 1 hour for dinner, more if time allows

   For post-dinner drinks, grab a Lyft to take you into the warehouse district for the most exclusive speakeasy of them all, the Office (must have reservations!)

   With an 8pm reservation, expect to spend at least 2-3 hours at the Office

   And you can’t end a day in Chicago without some music, so after the Office, grab a Lyft to the Green Mill for some jazz

   We found the crowds were thin on Sunday night at the Green Mill, but that didn’t dampen the energy of the jazz trio that were playing! And the best part was a cover charge of $5!

   Call it a night and get some sleep before you fly out of Chicago the following Monday morning!

Do you love Chicago and have additional insider tips to offer? Let me know in the comments!

Happy Exploring!

~ Trupti

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