Chicago: A 4-day itinerary and more..

Chicago is amongst our favorite cities in the US-history, museums, walking tours, food, shopping, Broadways, lakeshore, and a beautiful skyline, it has it all. The best time to go there is the summer (March-September); the winters are bitingly cold. Having been there several times for times mainly for conferences, here is a 4-day itinerary suggestion, as also multiple add-ons if you have more time.

General tips

Select a hotel close to the Art Institute/ Dusable Bridge area on Michigan Ave. We stayed at Congress Plaza (good for the price and location); always request for a room with the lake view/ Michigan Ave view at the time of booking.

– We’ll enlist the restaurants we liked at the end (all around Michigan Ave); but the list is not even close to exhaustive in this foodie paradise. We are sure you will explore and experiment and perhaps add a few suggestions in the comments section for the next time we visit Chicago!

– The museums etc. are often quite crowded (especially if you travel over a long weekend) and the entry line can go upto half an hour; we would recommend purchasing tickets online/ using a Beat the Line pass in such cases. The City Passes are a good option.

– There are three confusing options for city passes. In brief,

  1. The Chicago City Pass allows admission into 5 out of 7 predefined attractions.
  2. The Go Chicago (all-inclusive) Pass gives you access to 26 different attractions for 1-5 days depending on which card you purchase; it is great for those who would not be spending a lot of time per place.
  3. The Chicago Explorer Pass lets you go to 3-5 destinations of your choice amongst 28 attractions; the advantage is that you don’t need to pre select your choices giving you more flexibility. It is good if you can preplan a bit and bundle the most expensive tickets into the pass.

Always remember that these passes allow fast unrestricted admission in most places (highest priced ticket), but if you are planning to purchase a lower cost ticket, there may not be much of a saving. For example, at the time of writing this blog, there are three ticket options for Adler Planetarium; a $12 ticket which doesn’t cover any shows, a $25 ticket which covers one show, and an all-inclusive $35 ticket. The passes give you the $35 ticket.

– Public transport in Chicago is terrific and most of the attractions are within walking distance; don’t worry much about transit.

– We would highly recommend reading the acclaimed ‘The Devil in the White City’ before going to Chicago; it’s a fascinating and award-winning account of the historic Chicago world fair of 1893 which brought this city to the limelight. The architectural tour and the downtown area will make much more historic sense if you have read the book.

As usual, we are sharing our itinerary on our google maps page. Here is the link: Select the label ‘Chicago’.


Day 1: Art Institute of Chicago

Land early morning to make the most of the day. Depending on the time and logistics, you could either go to your place of stay or go directly to the Art Institute of Chicago and keep your luggage in the cloak room. The Art Institute is amongst the top three museums in the world and not something to be missed. Seeing it can easily take 4 hours to an entire day depending on your level of interest. There are audio guides available, and multiple complimentary tours happen on a daily basis focusing on certain pieces of work (always make it a point to ask about the timings of these tours at the Information Center and then plan your day accordingly). Do not miss our personal favorites, the Old Guitarist by Van Gogh, the Thorn miniature rooms, a sculpture called the Solitude of the Soul (we loved the explanation behind it, but not giving it away!), and another amazing sculpture called the Freedman, a black man just freed from his shackles sitting in a slightly ‘Thinker’esque manner, but only much more powerful!

If you finish early, you may want to sneak a small nap in the hotel before heading out in the evening. Otherwise, explore the city and head to the Skydeck or 360 Chicago (formerly Hancock Observatory) for checking out the city’s famous skyline in the evening. If that’s not your cup of tea, just head to the nearby Buckingham fountain, one of the largest fountains in the world, and enjoy the hourly light show.

Day 2: Walking tours

There are several amazing free walking tours on Chicago. We went along with Free Tours by Foot and would highly recommend it; another option is Free Chicago Walking Tours. Both have a 5 star rating on tripadvisor as of May 2017. We learned a lot about the city and its history thanks to the two walking tours we joined. Another option is to select paid walking tours offered by the Chicago Architecture Foundation.

The first tour we recommend is the Loop and Millenium Park tour, usually starting at 10.00 am. It covers major landmarks including the Chicago Theatre and the Marshall Fields store (now Macys) with its famed tiffany mosaic ceiling, and ends at the Bean and the Millenium Park. Enjoy some time relaxing and clicking snaps Anish Kapoor’s iconic structure (we don’t feel the need to write anything on it!). If you are with kids, the play area at the Maggie Daley park is a must see.


The Bean!

You can spend the rest of the afternoon exploring downtown Chicago and the Magnificent Mile. Then go ahead for the Chicago Riverwalk and History tour in the evening (it usually starts at 6.00 or 7.00 pm). This tour gives more insight into the history of Chicago as also a bit of an overview of its architecture. We understood the subsequent Architecture tour much better due to the orientation we had thanks to this tour. Our favorite tit-bit was the 150 labeled stones of the Chicago Tribune building, which have been collected from different parts of the world (read more at ). These include stones from all 50 American states, and from various important cities and monuments including and Great Wall of China and the Taj Mahal (yeah; it wasn’t strictly illegal to do that at the Tribunal’s time).

The Trump Tower was another interesting structure; don’t prejudge it by its name. It was designed by Adrian Smith (who is also the architect of Burj Khalifa), and it’s the multilevel terraces are a fitting tribute to the other surrounding buildings which form the history of this fantastic city.

The good thing with the walking tours is that since there are many quality ones offered by different companies, you can pick and choose the one that is convenient time wise. So feel free to alter the itinerary by choosing the other companies mentioned.

Day 3: Fields museum/ Shedd aquarium/ Adler planetarium

If you want to have a leisurely day, explore one of these three and leave the other/s to the next day. If you plan on covering two, this day may get busy and it would be a good idea to begin early. The Fields museum is famous as the one featured in ‘Night at the Museum’. Its other claim to fame is of course Sue, the world’s largest preserved T Rex skeleton. The museum is however otherwise relatively similar to the museums of Natural History at Washington DC or New York; you may get a déjà vu if you have been to either of them. We have been to the Shedd aquarium, and it houses an exhaustive collection of marine life (the jelly fish exhibit, if it still exists, was breathtaking). We haven’t been to the Adler planetarium personally, but it has got great reviews as well. Take a call based on what you like; you can easily explore two of these three attractions if you time it well (2-3 hours each). Do take time out to soak in a view of the city skyline from the Planetarium; it’s beautiful.

In the evening, catch the Architecture boat tour. The most famous and well rated is the one offered by the Chicago Architecture Foundation (5 stars on TripAdvisor); however others by Shoreline, Chicago Line Cruises and Wendella are also excellent (4.5 stars each on TripAdvisor) and slightly cheaper. Enjoy the tour and photography!

If the tour begins and ends at the Navy Pier, you may try the Centennial Wheel (Ferris wheel) as well. After all, Chicago is the birthplace of the Ferris wheel!

This architectural boat tour is an absolute must do. The sunset time would be ideal as it gives a view of the city in both daylight and the night sky. You must book the tickets early, as these sell out real early.

Architecture tour Chicago

A view of the skyline from our boat

Day 4: Lots of options!

Depending on your interests and the time of your flight there are multiple options for spending the day. You can further explore/ shop at downtown Chicago, go back to see the aquarium/museum/planetarium (we had once used the cloak room at Field Museum to keep our luggage and taken a flight directly after the museum), catch a food tour or the gangster tour, or just relax and enjoy the parks. Many more options are listed below: take your pick.

For the repeat visitor

It being Chicago, many of you might be repeat visitors and have already seen some of these attractions. Here are a few more suggestions.

– The Graceland cemetery: This houses the graves of many famous Chicagoans, including Daniel Burnham. Make it point to take a map of the cemetery before you start exploring. We loved it even more because we had a close Chicagoan friend who gave us a lot of insight into the different people resting at the cemetery. Having read Devil in the White City, it felt as if we were actually walking through that era. We have heard this place is also beautiful in the winters.

– Museum of Science and Industry: Apart from being a very interesting museum, it is one of the few surviving buildings from the world fair (it previously housed the Field museum before it was moved), and is next to Jackson Park, the original venue of the fair. Fun fact: The other building to have still survived is the World’s Congress Building which was built away from the fair site and now houses the Art Institute of Chicago!

– Catch the Chicago Bulls play at the United Center.

– Enjoy the Broadway you always wanted to see.

– Head to the Lincoln Park Zoo.


Here is a list of what we tried and loved.

– Deep dish pizza: There are only two reactions to the famous Chicago deep dish pizza; you either love it or you hate it. Either ways, it is worth a try. It takes around 40 minutes to make, so be sure you have enough time. Several pizza chains claim to make the best deep dish pizza in Chicago; would recommend going to the one most conveniently located. We tried the one at Giordano’s; one of us loved it and the other wasn’t too impressed.

– Firecakes Donuts: This is by far the best donut place we have been to, ever. Extremely versatile menu with many interesting flavors; a must go.

– Magnolia bakery: A branch of the original Magnolia bakery near Rockefeller Center in Manhattan, its banana pudding is to die for.

– Quartino Ristorante: A nice Italian place with great food; highly recommended.

– Ghirardelli Chocolate Café: Need we say more?!

– Naf Naf Grill: Think of a Greek Chipotle. It relatively cheap and good quality; great for a fast meal.

– Naansense: Great for a quick casual Indian bite.

Chicago is one of those cities we will be visiting again- so please drop in your suggestions and recommendations below and we will make it a point to tell us how you enjoyed it.


One thought on “Chicago: A 4-day itinerary and more..

  1. Pingback: RSNA for the first-timer: Making the most of it – Cafe Roentgen

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