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Top 5 Things To Do In Chicago

Updated on May 2, 2012

Well, maybe not the top five things to do for everyone, but the top five things for a Coloradoan. Okay, maybe not even the top five things for a Coloradoan, but definitely five things you must consider doing if you're going to visit Chicago. And if you haven't visited Chicago before, or even if you have, you should, because it's a great city filled with (mostly) friendly people and a plethora of things to do and see and experience!

1. Architectural Boat Tour

There are tours aplenty in Chicago - walking tours, air tours, boat tours, bus tours; tours you can probably design and tailor to fit exactly what you want. I HIGHLY recommend a boat tour. There are several types of boat tours you can take - general, architectural, night fireworks, night cruise, dinner cruise, the list goes on - but I think the architectural type of tour offers the best - you get to be on the water, while at the same time learning the incredible history of Chicago through the architecture of the city. And let me tell you that it's so fun and amazing! I love learning the historical aspect of cities I visit, it helps me feel more connected to each place in a different way than just to say, "Oh yeah, I've been to Chicago." I am now able to recognize different buildings and landmarks of Chicago and can identify how they are unique to the city and have contributed to it's growth and development. I took the architectural boat tour with my mother, sister, and one-year old niece, and it was so much fun! Depending on how you plan your day, the first tour of the day seemed to be the best, it wasn't quite as crowded, and we were done with the tour by the time the heat of the day really hit. It's fairly affordable, between $25 and $35, and usually runs about an hour long and is absolutely worth it. We grabbed breakfast and a cup of coffee before we left, then enjoyed the sights and sounds as we continued to savor our coffee on the beautiful waterways of Chicago. I suggest planning on taking hats, sunglasses, sunscreen, cameras and bottles of water; we went during the summer, so obviously plan according to the season. I mentioned my niece was one years old, and it wasn't too much work having a small child with us. She was able to run around (early tour = not as many people = more space to move) and not be confined to a small space where she would have likely become bored and fussy. My sister was also able to still enjoy the tour without having to worry too much about keeping her daughter entertained. That said, an architectural boat tour should definitely be on your list of things to do in Chicago!

2. Giordanos Pizza

It is a fact that there are pizza debates: New York style versus Chicago Style; thin crust versus deep dish. Once you've narrowed it down and picked Chicago style (and are actually in Chicago), the debate becomes: Giordano's versus Gino's. Everybody has a favorite, everybody picks a side. Let me decide for you. Giordano's. All. The. Way. After you've had a delightful boat tour and have gotten your "land legs" back, you're going to be hungry. What better way to satisfy your hunger than with a delicious, decadent, mouth-watering piece of Giordano's Chicago-style deep-dish pizza?! It doesn't get much better than that. Seriously. I often feel the need to make a quick trip back to Chicago just so I can satisfy this craving! There are locations throughout Chicago, and each one I've been to (yes, more than one!) has been a delightful experience. If you've never tried Chicago deep-dish before, the pizza is set in a, what else?, deep dish. It's made a little upside down from the usual however, with layers of cheese on top of the dough, then your choice of toppings, then the rich, flavorful marina sauce smothers the entire pie. My perfect pizza is pepperoni, green peppers and onions, but as with any food you are free to choose your toppings and style. Let me just say that you would be remiss to not try while you are in Chicago.

The Bean, Millennium Park
The Bean, Millennium Park
The Bean, Millennium Park
The Bean, Millennium Park
Splash fountain in Millennium Park
Splash fountain in Millennium Park

3. Millenium Park

Millennium Park is a great tourist-y place to find yourself. It is home to Cloud Gate, the sculpture also affectionately known as "The Bean," a small ice skating rink in winter, the Jay Pritzker Pavilion, gardens and more. You'll definitely want to get your picture with The Bean, capturing your reflection and, from different angles, the reflection of the skyline around you. Stop at a hot dog stand and try a famous Chicago-style hot dog (yes, there are a lot of Chicago-style foods, and yes, you will be missing out if you don't try them) and a refreshing cup of lemonade. Wander through the beautifully kept gardens and admire the flora and fauna, or find an out-of-the-way bench and settle in to people-watch. Check the local calendar for concerts and/or music festivals at the Jay Pritzker Pavilion. And if you've got your kids with you, there's a great splash fountain for them to play and cool off in, with the water coming out of "towers" with images that continually change! Millennium Park is a great place to rest from shopping and sight-seeing, and best of all? It's free! Check it out here:

Water Tower & John Hancock Tower
Water Tower & John Hancock Tower
Ghiradelli's "Gold Rush"
Ghiradelli's "Gold Rush"
View from the bridge on the Magnificent Mile
View from the bridge on the Magnificent Mile
View from the bridge on the Magnificent Mile
View from the bridge on the Magnificent Mile

4. The "Magnificent Mile"

The Magnificent Mile, also known as Michigan Avenue, is a miles worth of magnificent shopping. I would compare it to 5th Ave. in New York City. For someone such as myself on a budget, it's a great way to get a different feel of the city at low-to-no-cost, but a great experience of window shopping and enjoying the sights and sounds of Chicago. Depending on the shoes you're wearing, and how much walking you like to do, it's a fun walk. I suggest beginning at the North end of Michigan Ave., and making a day of it!

You can start out by going to the John Hancock Tower/Observatory and getting the beautiful birds-eye view of the city. Admission starts at around $15 and goes up to around $30, I personally preferred The John Hancock Observatory over the Sears/Willis Tower, partially because of the location and also because it seemed to be a better overall experience.

After you've had your fill of sky-high views, exit the building and head towards the Magnificent Mile. You can actually walk from the John Hancock Observatory (JHO)all the way to Millennium Park and back if you so desire, which I have done and it wasn't too taxing, probably because of all the stops along the way! However, even if you choose to stay at the north end of the Magnificent Mile there are still plenty of shops and things to keep your attention.

After the JHO it's worth a stop to check out the Water Tower and Water Tower Museum. Admission is free, and it's another aspect to the history of Chicago, as it is one of the few buildings that survived the Great Chicago Fire of 1871. It's a beautiful building that testifies to the ever-changing architecture of Chicago and the resilience of the city.

Once you've toured the Water Tower, there is a great little Starbucks towards the East of the Water Tower. What makes this particular Starbucks so great is that it's got such character! The store is located in what was once an apartment, so the layout and ambiance of the coffee shop is very unique, even for Starbucks. I apologize for not remembering what street it is on, but if you've got time and don't mind walking around exploring it's a fun little side trip.

In the same area as the Water Tower is Ghiradelli's! Who doesn't want to stop for an ice cream break?! And since you're on vacation and have already partaken of decadent pizza and world-famous hot dogs, why not top it off with a bowl of rich and creamy Ghiradelli's ice cream? Or chocolate and candy? It's a fun stop to sit on the patio and again observe the comings and goings of the tourists and citizens alike.

Across the way (to the south) from Ghiradelli's is Chicago's American Girl Place, that is so big and beautiful it houses at least three floors of fun! Do you have a daughter? A granddaughter? A young sister? A niece? Are you vacationing with a woman? If you answered "yes" to any of the above questions then it's definitely worth a stop in the American Girl Place. Whether you're window shopping or seriously looking to purchase, it's a fun store overflowing with girly frills and thrills that women of every age will enjoy. I can't wait until my nieces are old enough to appreciate (and take care of!) their own American Girl dolls; I guess I'd better start saving now! Check it out here, and do some shopping online!

If you'd still like to see more of the Magnificent Mile, head south and start window shopping! Even if you only get as far as the bridge, it's a fun walk. And an added bonus is in the summer there are usually street performers at different intervals that are fun to watch and listen to, so don't hesitate to do so and then tip! You also never know what movie will be filming in Chicago while you're there - my mom and I saw Vince Vaughn and Paul Giamatti filming a scene for "Fred Claus," now that movie is endeared to me because I WAS THERE!!!


So I couldn't narrow down a fifth something to do, there are just too many wonderful and exciting things to occupy your time in Chicago. You may have figured out that I travel on a budget, which I think is great! I don't feel like I have ever missed out on anything in the places I visit because of a financial constraint. That said, check Chicago's calendar for free days! The Museum of Natural History and Shedd Aquarium, just to name two, offer free days to the public, and if you time your visit right you may be able to take advantage of the free days. However, keep in mind that along with your travel companions, there will also be hundreds of other tourists and Chicago residents also taking up the free day offer, so things could get very crowded very quickly. Be forewarned.

I recommend using public transportation, but only to the extent to which it is convenient and within your personal comfort zone. Most big cities offer one-day to seven-day transit passes that cover buses, trains, and in Chicago, the EL. Grab a map, plot out your course, and away you go! I have found that most residents are eager and willing to help if you need help with directions or have questions which train or bus to take where. Public transportation also gives you a taste of the city on a more personal level and allows you to notice parts of the city that you might otherwise have bypassed. I love to keep my transit passes once I'm home and use them as bookmarks - it's a cheap souvenir and reminds me of wonderful times I've had away from home. If you prefer taxi's, we found that an average fare was around $20 plus tip to most of the high-tourist traffic areas.

Depending on where you stay in Chicago, it's fun to find a local coffee shop or cafe and visit a few times during the course of your visit. It's a great way to try more localized (and maybe not so famous) cuisine while getting a feel for the different neighborhoods in Chicago.

And finally, add some off-broadway culture to your Chicago experience! Find out what shows are playing in Chicago and partake! My mother and I saw "Wicked" for the first time in Chicago, and to date it's still been one of the best theater performances I've ever seen! Check it out if you can, it's definitely worth a little splurge."Wicked" was playing at the beautiful and ornate Oriental Theater, and even if "Wicked" is no longer showing there, the theater itself is beautiful enough to stop and visit.

Until Next Time ...

I love Chicago. It's one of my favorite destinations and holds some of my favorite travel memories. There is so much to do, regardless of what season you travel in, that I think it would be very hard to have a bad trip, circumstances notwithstanding. If you're looking for someplace to visit this summer that you haven't been to yet, please consider Chicago, I don't think you will be disappointed. And if you've been to Chicago before, please don't let that stop you from going again. Every visit will be new and different, filled with fun surprises and unique experiences. So start saving, put it on the calendar, pull out some maps, make a list of "must-do activities" and make it happen!


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