My 8 Favorite Things to Do in Chicago

  • Chicago-Skyline from Signature Lounge

Anyone visiting Chicago will look up on some website, “things to do in chicago.” Inevitably most sites will tell you to go to Millennium Park, Willis Tower (formerly Sears), Navy Pier and take some sort of boat tour. I think some of those are great ideas and you should do them if you’ve never been to Chicago, however they are very touristy and not really what the every day Chicagoan does.

I like travel where you can do things that the locals do (pro-tip: Navy Pier is just not a good tourist attraction, I beg of you not to go)! If you’re looking for something a little deeper and only known by the locals, take some ideas off of my lists. These ideas are usually not mentioned on travel websites but they’re my favorite things to do in Chicago. I love local and non rushed ideas, and these things to do in Chicago will deliver a great experience.


SV’s 8 Favorite Things to Do in Chicago


Signature Lounge for Views and Drinks, Hancock Tower

I think the Signature Lounge is one of the most underrated things to do in Chicago because simply, the Hancock Tower isn’t the most popular tower to visit. However the great thing about the Signature Lounge is that you don’t have to pay to go up. You only pay for the drinks and the food that they serve. So you get to enjoy your view longer than you would at the Willis Tower where the only thing to do is look out. The drinks and food are expensive but it’s the price you pay for such a great view of the city and cheaper than going up the Willis Tower. I’ve been on summer days and cold, wet days and the view is always great. On a clear day you can see Indiana and Michigan!

To get into the Signature Lounge you need to go the Hancock Tower which is located on the northern end of Michigan Ave aka known as the Magnificent Mile. If you’re staying anywhere around Michigan Ave you could take one of the many buses that go up and down Michigan or simply take a taxi, they will know where it is. Once there you need to go on the right side of the Tower, near Cheese Cake Factory, enter into the doors, and then go to the right. You’ll see a sign that says Signature Lounger and it’s absolutely free to go up! One of the most beautiful things to do in Chicago!

Chicago-Skyline from Signature Lounge

(view from the Signature Lounge)

Brunch, Coffee and a Cinnamon Roll at Ann Sather

If you like huge portions of breakfast food, coffee and a cinnamon roll, than you must go to Ann Sather. They have locations in Lakeview and Andersonville (the original is there), and serve some of the best breakfast food in the city. You may have to go early though because it can get very crowded. They don’t serve alcohol if you’re hoping for that! Ann Sather is 50 years old and is known for their Swedish food and is one of my most favorite things to do in Chicago.

There are 2 Ann Sather’s in Lakeview. You could take the L (red line) to get to all 3 of them and they are generally in walking distance from L stops. Taxis from downtown to Lakeview are going to cost around 15 dollars so budget in for that, if you don’t feel like taking public transportation. There are also plenty of buses like the 36 or 151 that go from downtown to Lakeview. Two excellent things to do in Chicago!

Edit: The original Ann Sather’s in Andersonville has since closed since I visited it last summer.

Original Ann Sather things to do in Chicago

A Bicycle Ride through Lincoln Park

Lincoln Park has to be one of the best parts about Chicago, in terms of natural beauty. The park stretches from the southern end of Chicago all the way to the northern limits. Now Chicago has started to place bicycles for people to rent, a perfect way to see much of Lincoln Park. Some of the best places to visit would be in Lakeview and Lincoln Park (the neighborhood), because there is plenty of room to have a picnic or plenty of restaurants near by so that you can easily pick up a lunch. Also they’re a lot of bike rentals in the area. Lincoln Park also has it’s very own zoo and conservatory, all of which are free.

To get to Lincoln Park you just need to head east. It’s the green part that borders the city and Lake Michigan. I feel the best parts of Lincoln Park are in Lakeview and Lincoln Park, the neighborhood. Buses like the 151 will take you through portions of Lincoln Park and it leaves from downtown. One of the most peaceful things to do in Chicago.

Lincoln Park Tree

Deep Dish Pizza at an Established Pizzeria

I normally don’t promote people to eat food that isn’t so great for them, but I will make exceptions. An experience that non-locals must have is to eat at a local and well established pizzeria. And they must order a deep dish pizza because that is Chicago style. The reason I didn’t list just one pizzeria is because they’re a couple of well-known places to go.

For instance, Ginos East and Giordianos are probably the most famous and right fully so. Their deep dish pizzas are amazing and well worth the long lines they usually have on the weekend. There are many Ginos East and Giordianos in the city and they’re some downtown if that is where you’re staying. Also I would recommend Pequod’s, Nancy’s and Mista Pizza. Pequod’s is in Lincoln Park while Nancy’s and Mista Pizza are in Lakeview! Check the websites for directions and locations! One of the best eating things to do in Chicago!

Giordianos Deep Dish Pizza

A Night Drinking on Halsted

Lakeview is party central because of how many young people live in the neighborhood. They are an ample amount of bars on Broadway and near Wrigleyville but if you’re gay or you just want to have a good time, you should go to Halsted Street in Boystown. There are about 50 bars in the area and all of them are gay or gay friendly. If you’re looking for a good time than this is the area you’ll want to be in. There is Roscoes (one of the oldest bars in the area), SideTracks, Elixir, Scarlett, Minibar and the list goes on; easily one of my favorite things to do in Chicago!

If you’re coming from downtown I suggest taking a taxi but you could take the number 8 which goes right up Halsted or you could take the L specifically the red or brown line and get off at Belmont. You then walk a couple of blocks to the east until you’re on Halsted, then walk north.

Halsted Street with Rainbow Poles

Shopping on Michigan Ave and then on Rush Street

Okay so I’ll admit that this is a very touristy thing but doesn’t really matter because you’ll also see local Chicagoans on Michigan Ave shopping. This is where all the major department stores are and all the name brands. It’s an enjoyable street to walk, even in the winter time, because you are never very cold for a long period!

If you love shopping or just need an area to walk around than I suggest starting at the Chicago River, where all the boat tours start and where the Wrigley Tower is, and then walk north. Once you hit Walton Street or Oak street take a left and enjoying walking down a really lovely part of Chicago (expensive… very!). You can even stop to get a delicious and over priced cupcake on Walton at famous Sprinkles. Once you hit Rush street you can have lunch at Tavern on Rush or shop in some of the most expensive stores in Chicago. This will easily be one of your favorite things to do in Chicago.

Weekend in Chicago - St Patricks Day Parade

Afternoon at One of Chicago’s Beaches

Okay so you can only really do this when it’s warm but still that is when most tourists come! So when you come to Chicago definitely pack a bathing suit!! I know that sounds weird but Chicago actually does have beaches and they are actually pretty nice. Lake Michigan is always cold but it can be very warm in the summer that you won’t mind taking a dip into the Lake. It’s weird to have this urban landscape while you lay in your bathing suit watching people play volleyball in the hot sand.

Which beaches should you go to? Well there are beaches up and down Chicago but the most famous ones are at LaSalle and Lake Shore Drive in Lincoln Park (this is where all the families and straight people go). Or the further north and the lesser known Hollywood Beach or Kathy Osterman Beach or aka the Gay Beach. However you can also find a little beach near Lake Shore and Oak street in Near North Side but it’s quite small! One of the most unusual things to do in Chicago.

Chicago Beach Illinois

Tea Time at the Drake

And finally Tea Time at the Drake. The Drake Hotel is located in Near North Side and has an awesome view overlooking Lake Michigan and Lake Shore Drive. It’s also an institution and classic hotel in Chicago. So if you’re walking up and down Michigan Ave and you need a break I recommend tea time at the Drake in their Palm Court. Of course they serve specialty tea but they also serve finger sandwiches, scones and sparkling wine. Tea Time is served in the elegant Palm Court with a harpist playing in the background. It’s served from 1 – 5 pm daily! I just read that the Drake Hotel is also introducing Monday Movie nights on the second and fourth monday of every month. It’s all classical movies and you can check on their website what movie they are playing.

The Drake is located on the northern most part of Michigan Ave where Michigan merges with Lake Shore Drive. There are multiple buses that will shuttle you from the Loop, up and down Michigan Ave or you could just simply walk. One of the most relaxing things to do in Chicago.

Tea Time at the Drake



I hope I’ve given some new ideas and a unique perspective if you’re visiting Chicago. There are so many things to do that it can get over whelming and sometimes you need to get away from the touristy parts. I also have a page that you can visit for even more ideas on what to do in Chicago here! Hope you enjoy your visit and have some new things to do in Chicago!




images by: shawnvoyage, araceli, max

By | 2017-08-23T20:00:43+00:00 April 3rd, 2014|