8 Best Things To Do in Chicago, Illinois (for Two Days)

I’ve always wondered what it was like to visit the midwest. There was a city that is well talked-about and a city that I’ve always had a serious curiosity for. Chicago in the midwest state of Illinois provided that opportunity for me. Back in January, I visited Chicago in hopes of celebrating my birthday in it by exploring the city.

Exploring a city for a birthday may not be everyone’s cup of tea but since last year when I saw the Grand Canyon for the first time before I moved out here, it was something I decided I want to stick to. Parties and dinner parties felt overrated for me and the older I get, the more I am running out of ideas of what special things to do for my birthday.

As a winter baby born in January, I don’t let weather affect whether or not I’d have fun exploring a city. I visited Chicago in the midst of its cold winter season and I know it may not be ideal for everyone, but I think everyone should understand (and take note of) that the times when less people are visiting, tickets will be relatively lower in price than peak season. That’s the best time to enjoy a trip and how could I say no to cheap round trip flight tickets to a city I’ve never visited before?!

Chicago turned out to be one of my most favorite cities that I’ve visited thus far in the United States. Nicknamed as “The Windy City” and “Chi-Town”, this city is no joke when it comes to heavy winds reflecting from its neighboring body of water, Lake Michigan. Its also home to the second tallest skyscraper in the nation, classical and old fashioned architect that amazes its millions of visitors yearly, the Cubs and the Bears that is truly loved by its Chicagoans, and deep-dish pizza where Chicago claims to be one of the best pizza places you’ll truly indulge in. In comparison to New York City, Downtown Chicago takes one of the top places for having the most beautiful skyscrapers that will make you feel like you’re lost in a city. There is a lot of similarities with New York City to Chicago but it’s also reminiscent to me with Toronto and I think these two cities put together nearly create the atmosphere that Chicago provides. 

If you’re planning to visit Chicago or are already convinced to, here are a list of things to do and recap of things I did when I visited Chicago for only 2 days. I do hope that when I get to visit this city again, it would be in the summer as I was told by the locals it’ll be much more fun. This simple guide was crafted for you if you’re planning on also visiting in a short amount of time (it’ll make as a great weekend trip!) and/or visiting it during winter, which is probably one of the most affordable times to visit the city.

1. Visit Grant Park.

When I booked my hotel, I found a decent hotel called Best Western Grant Park Hotel to stay at right by Grant Park, so everything was great walking distance especially during the winter. Grant Park is a large urban park with a number of notable features that I highly suggest below too. It’s a whole section that is 312.98 acres long and its location is right in Chicago’s central business district in the Loop community area. Think of it like New York City’s Central Park of Chicago. While the park encompasses features like Millennium Park and the Museum Campus, Grant Park is also the scene for gardens and sports areas and hosts numerous festivals of Chicago.

As one of Chicago’s first parks, this park was actually first named Lake Park, but it was renamed to Grant Park to honor the 18th President of the United States, Ulysses S. Grant.

2. Go to Millennium Park: Go ice skating and marvel at Cloud Gate/The Bean.

The famous park of Chicago, considered as a smaller part of Grant Park, and the second most well-known attraction downtown is Millennium Park! Millennium Park consists of public art installations, marvelous architecture, and open space that is perfect for socialization.

At 25-acres, this park has the Lurie Garden, a green space that keeps the nature alive through the city and Crown Fountain, large-scale digital screens that project the everyday faces of Chicagoans with fountains that are fun to roam in. Then there’s the Cloud Gate, a sculpture by Sir Anish Kapoor that is made up of 168 stainless steel plates welded together. It’s such an astonishing art piece because the surface of the steel is smoothly polished with no visible evidence of the seams. It’s also famously called The Bean and was inspired by liquid mercury, reflecting the city’s skyline onto the art piece and creating a distort illusion when you look into it. I highly suggest you take a visit at this because of the process behind it and the creative result of it.

During the winter in Millennium Park, ice skating seems to be one of the more viable fun options. In the Millennium Park McCormick Tribune Ice Rink, you can rent ice skates and ice skate surrounded by Chicago’s stupendous skyscrapers. On my birthday, I ice skated here and since I’ve always wanted to do that in Millennium Park, I’ll always consider it as a memorable day. To me, Chicago has the most aesthetically looking skyscrapers I’ve seen compared to other US cities I’ve traveled to, so ice skating around them was a refreshing view that got me very excited.

3. Do the Skydeck in the Willis Tower.

A visit to Chicago would not be complete without trying to go to the second tallest building in North America, the Willis Tower (formerly known as the Sears Tower, so if you hear about this too — they’re the same). Although, there is usually a long waiting time to get inside the tower, which can take hours, so I don’t blame you if you’d like to skip this. The best time to go check it out is in the very morning, with little to no waiting time. My mom, who came to Chicago with me, and I waited two hours standing up in a line to be able to grab a spot to be able to see the Willis Tower from atop — to us, it was so worth it.

Inside the Willis Tower, there is the Skydeck. The Skydeck is the company that allows you to go to the 103rd floor or above at 1,353 ft up. The basic admission for adults is $25 and for the youth (ages 3-11), it is $17. Children under 3 years old are free! Part of your admission will allow you to experience The Ledge. Skydeck’s Ledge is a glass floor extending out of the 103rd floor where you can look down from your feet to see the highway and buildings below you. It’s a thrilling experience and quite an adrenaline. It made me feel the effects of vertigo right away, even though I knew I was safe regardless. My mom did a short scream and pulled onto my sweater when she hopped on it haha.

Since we waited a while to get inside the Willis Tower, we did not get to see the views from outside the Willis Tower during the day, which I originally planned. It got dark by the time we rode elevators to the top (you have to ride a couple of elevators and switch off from them to finally get to the 103rd floor). The night views blew my mind though and it provided a beautiful scenic, yet peaceful viewing of the Chicago skyline. From afar, you can see Lake Michigan with numerous glaring lights reflecting from the buildings.

4. Try Chicago’s deep dish pizza and Chicago-style hot dog.

Everyone raves about the famous deep dish pizza from Chicago, and it’s hard not to see why when you finally get an authentic taste of it. The deep dish pizza is everything exaggerated in a pie: chunky tomato sauce, a buttery crust, and toppings that are much preferred in fillings with mozzarella cheese that is thick and stretchy. It’s basically pizza taken on a level of extra. Many consider eating the deep dish pizza as a local experience to dine with. There are many restaurants that make their deep dish pizza homemade in the kitchen and freshly baked out of the oven; I mean who doesn’t prefer it that way anyways?

Some of the best-known restaurants to where you should try this pizza are Lou Malnati’s Pizzeria, Giordano’s, The Art of Pizza, Bella Bacino’s, Gino’s East, just to name a few. We opted for Giordano’s pizza while we were waiting to go inside the Willis Tower, which served convenient to us since it was around the corner of the Willis Tower. With a small birthday celebration in the restaurant, I was greeted with a free tiramisu cake and a candle after having my ultra can’t-be-guilty-of-it-because-it’s-so-damn-good deep dish pizza.

If pizza is not your thing and maybe hot dogs are, Chicago is also known for their Chicago-style hot dogs. What is a Chicago-style hot dog? It’s a regular all-beef hot dog with yellow mustard, chopped onions, pickle sport peppers, sweet green pickle relish, celery salt, and tomato wedges. I think it had already occurred to you that Chicago likes to do things big on their food. Although I did not get to try this back then, you can find them at these spots: Portillo’s, Wolfy’s, Chicago’s Dog House, Gene and Judes, Byron’s, just to name a few.

My little birthday tiramisu cake!

5. Walk by foot to really see Downtown Chicago and take the CTA buses to get from place to place.

If there’s anything I will highly and always recommend when you travel to a new city, it’s to try the experience of walking by foot! You’ll find places you might want to walk into out of curiosity or see Chicago’s massive skyscrapers hanging above your head. You also will get a close glimpse in interacting with the locals when you’re traveling within Chicago’s sections by foot. The experience as a whole is different when you can walk and a lot of places is walking distance — from my hotel, I was able to easily walk 7 minutes to the CTA station. In fact, if I didn’t speak with the locals there, I wouldn’t have known there’s the CTA (Chicago Transit Authority) bus/train that you can use as transportation to make your way into Chicago’s places in the most affordable way. For a $10 fare pass that guarantees all-day access, I was able to ride the bus to different divisions of Downtown Chicago. Check out www.TransitChicago.com for more information on taking the CTA buses or trains.

6. Visit a museum: Try The Art Institute of Chicago.

Where is one of America’s oldest and largest art museums? Right here in Chicago! The Art Institute of Chicago is located in Grant Park and it was founded in 1879. As Chicago became one of my favorite US cities, this museum is also one of my most favorite art museums. An adult admission fee is $25 but $20 for Chicago residents and $22 for Illinois residents. There are also admissions for seniors, students, and teens, but children and members get free admissions!

The Art Institute of Chicago is recognizable from the outside with the iconic green lion statues by the entrance and these lions have stood there since 1894, created by artist Edward Kemeys. When you go inside, you’ll be amazed by the ‘royal’ ambiance of the lobby with its Corinthian pillars that reflect the building’s exterior. The museum is huge, but don’t be overwhelmed. Make sure you have plenty of time (about 2-3 hours) to thoroughly enjoy it and see a lot of the art exhibits.

One of the reasons why The Art Institute of Chicago is my favorites is because it possesses so much of the original work by well-known artists that I’ve read through my art classes and textbooks. I am fortunate to have seen an up-close of Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte”, Grant Wood’s “American Gothic”, Claude Monet’s “Water Lilies”, Vincent Van Gogh’s “Self-Portrait”, Georgia O’Keeffe’s “Sky Above Clouds IV”, just to name a few of my favorites. I was also intrigued by the antique section that features antique furniture from European and Asian countries as old as the 1700s.

There is just endless artwork to witness in the museum from contemporary to European to cultural pieces, and it is worth every cent of your admission. Not to mention, they have an awesome gift shop full of fun trinkets inspired by the artwork displayed in there.

7. Try one or two of Chicago’s local shops: Such as Stan’s Donuts and Coffee.

I think one of the most fun parts of going to cities is discovering a lot of local businesses and I’m a true supporter of those mom-and-pop shops and businesses only found specifically in that city/state. Whether it’s food, entertainment, or merchandise, local shops will provide you that unique Chicagoan experience.

One shop that I had to return to more than once and that I discovered from a short walk from my hotel is Stan’s Donuts and Coffee. They started out in Chicago in 1963 and has served celebrities like Elizabeth Taylor and Steve McQueen. I’m not only obsessed with their pink and green diner themed cafe shop that displays a multitude of multi-colored KitchenAids (imagine owning a collection like that?!) and their ultra cute packaging, but their coffee and donuts are heavenly!!! I love trying their frappe and Biscoff Banana Pocket donut (their pocket donuts are the best and I wish I can find something like it again!).

8. Do the hop-on and hop-off bus tour to get the FULL Chicago experience: Experience BigBus.

If you really want to get an overview of Downtown Chicago, I recommend doing a BigBus tour and not only for Chicago, but if you’re visiting a major city in Europe, America, Middle East, and Asia-Pacific, try the hop-on and hop-off experience. For only $40.50 for an adult ticket, you have the opportunity to explore Chicago’s top attractions and can use their bus transportation to ride in-and-out of it for the day. There’s also a personal tour guide who will be on the bus to explain the places you’re viewing from the bus along with a plethora of interesting history. I always like to go to the top level of the bus especially since it gives you the best views with an open roof (sometimes, there’s a glass cover over it), but I’ll warn you, it’s kind of courageous torture to experience in the extreme cold, windy weather of Chicago in the winter.

In a BigBus, you’ll be wowed with all the iconic skyscrapers, an up-close view of Lake Michigan, and all the big attractions that make Chicago an interactive experience with Field Museum, John Hancock Center, Michigan Avenue Bridge, Navy Pier, Shedd Aquarium, Willis Tower, Adler Planetarium, Soldier Field, and Magnificent Mile. Magnificent Mile is a commercial district that is full of hundreds of luxurious and upscale shops and hotels, hip restaurants, and magnificent landmarks such as the historic Chicago Water Tower and Tribune Tower.

Of course, with only limited time to spend in Chicago, you may not be able to explore all of those, so my suggestion is to try to wake up early for the morning to get a lot of time from finding a BigBus stop and to do your exploring. You should also just find the places that really interest you to find it worthy to stop by at.


Want to save on some attractions? Try CityPASS!

The best way to do top tourist things in a city you’re exploring while saving (because paying for admission fees in each attraction ADDS UP!) is using a company that sells discounted tickets. I’ve personally used CityPASS in the past a few times and it always turned out to be a great experience and made me feel blessed to save.

Out of the several destinations they cover, Chicago is luckily one of those destinations! What kind of benefits can you get out of using CityPASS?

  • Save up to 50% in ticket sales compared to box office prices
  • Skip main entrance ticket lines at attractions
  • Have the eligibility to redeem vouchers within 6 months of purchase
  • Visit attractions at any available time at any order (the ticket is valid for 9 days)

If you’re interested in using CityPASS, click here to start purchasing so you can enjoy a nice activity-filled trip!


If you want to get more information on exploring the city of Chicago, Lonely Planet has this awesome guidebook with full-colored maps and pictures throughout the book, itineraries that will cater to your personal needs and interests, tips that will help you save money and time when getting around, reviews on eats, where to sleep, attractions, shops, and much more. It’s a great resource to everything you need to know.

Lonely Planet’s Chicago City Guide(comes as a print book, eBook, chapters, book + eBook)

The Best Western Grant Park Hotel is a nice, affordable hotel that I was very pleased to stay in. However, there are plenty of hotels you can find to stay according to your budget and style. Use this booking tool below to help you find the best hotel!


Note: This post includes affiliate links. You can read my full disclosure policy here. If you make a purchase from one of these links, I will earn a small commission but with no additional cost from you. Like most sites, my blog website needs compensation to keep it running, so thank you for supporting me to keep on helping!

Pin It!

This Post Has 5 Comments

  1. Ken Dowell

    I love Chicago as well but I’d hold off until springtime.

    1. from1girlto1world

      Yeah, Chicago seems like a better idea to visit until spring and summer time. It’s really cold to visit in the winter and to walk around in!

Tell me what you thought below!