Travel - Chicago

9 minute read


Summary: A walkthrough of my experience in Chicago. gallery:{photo}chicago

Chicago, Illinois, USA

Table of Contents

General Suggestions

Things to be added:

  1. sample itinerary

I’ve added to different sights, whether it is good for indoors (when weather is poor)! Look for the $\bold{[X]}$.

If you need airbnb (you’ll get a free $40 off):

If you need uber (you’ll get a free ride!):

If you need taxify (you’ll get a free $5 off!):

If you need lyft (you’ll get a free ride!):


To get to/from the airport, you can take the metro, which is only about $3. Else, you can take uber/lyft.

  1. O’Hare Airport:
    This is the main airport that is a lot larger.

  2. Midway Airport:
    This is the main airport that services Southwest.


1. Cloud Gate / Millennium Park:

This is the home of the infamous Chicago Bean. The entire area has very cool architecture, and there is a snake bridge that goes over the highway that leads to a park.

I would highly recommend coming to check out the Bean once during the day and once in the late afternoon. The different lights provide for a truly appreciative experience. If you’re into checking out cool parks, go to the playground that is across the snake bridge. There’s an incredible playground built for kids, but it’s a great experience to relive your childhood making your way through the slides, tree houses and swings.

2. Art Institute of Chicago:

Would highly recommend if you’re into art. A great collection.

3. Chicago Architecture River Tour:

This is advertised all over the city. A ticket costs ~$35 and you go on a large boat that will take you on a guided tour throughout the river and talk about some of the history of Chicago and its beautiful architecture.

Although the price seems hefty, it’s a great thing to try at least once (hell, I’ve gone twice and loved it both times). I would definitely recommend trying this in the warmer seasons because it can get unbearably cold outside on the boat deck.

4. Willis Tower / Sears Tower:

This was at one point the tallest building in the USA and houses the infamous glass cube. You’ve probably seen a bunch of your friends Instagram this. If you’re afraid of heights, it might not be the best idea. However, it definitely makes for a cool sight and is worth the trip at least once. It does cost quite a bit of money to go up.

5. Lincoln Park Zoo:

Apparently this is free, so why not.

6. Crown Fountain:

If you go to Cloud Gate, you just have to venture a bit south to reach this beautiful sight. It’s essentially a huge fountain that is great to take photos of.

7. Navy Pier:

This is a pier that you can walk around, which houses a ferris wheel and a bunch of other amusement park rides. It’s a great walk during the warmer seasons.

8. River Walk:

This incredible area is essentially a walkway along the river of Chicago. It takes you from the Trump Tower all the way down the river, and is an incredible place to walk during the daytime as well as night time!

Take note, that there is a closing time for the river walk at night (~11PM), so I would go around 9 if you want to grab some great night shots of Chicago!


Here, I briefly describe a couple of food places that are worth the HYPE. For locations, just use google, or yelp.

1. Deep Dish Pizza:

Everyone has heard about the infamous Chicago deep dish pizza. Well if you’re into pizza, meat, cheese and sauce, then it’s really worth the hype.

The places that are well worth the try are:

  1. Lou Malnati’s
  2. Giordano’s
  3. Pizzeria Uno

It’s hard to decide which one is the best, but for my personal preference I like them in this order because Lou generally has a better crust. It’s more crunchy.

2. Garrett’s Popcorn:

This is a famous popcorn place that sells all different kinds of popcorn. You name it; they probably have it. Everything from caramel, chocolate covered, to regular popcorn, Garrett’s has it all. This is great for souvenirs for friends/family/coworkers because they sell them either in traditional popcorn bags, or in to-go containers.

3. Purple Pig:

This is by far one of my most favorite restaurants in all of USA. It’s a tapas place (family style sharing of small plates), so definitely try to come with a group. There is generally a wait, so I would recommend putting your name down early around dinner opening, or lunch opening, and then possibly going and walking along the RiverWalk.

I’ll leave it to Yelp to advise you on what to eat because truly everything there is worth your money.

4. Girl on the Goat:

This is also by far one of my most favorite restaurants in all of USA. It’s a tapas place (family style sharing of small plates), so definitely try to come with a group. It’s slightly more upscale and more expensive then the Purple Pig.

I would advise MAKING A RESERVATION well before your trip. If you have a large group, there is no way you will get seated if you are only in town for a few days.

I’ll leave it to Yelp to advise you on what to eat because truly everything there is worth your money.

5. Wildberry Cafe:

This is my favorite brunch place. It’s right next to Cloud Gate / Millennium Park. Hands down, make sure you try their specialty pancakes and pretty much everything else on the menu is great. There will always be a wait, so you can put your name down and then go check out Millennium Park.

I’ll leave it to Yelp to advise you on the rest.


1. The Mid:

This is a night club that houses some DJs from time to time (e.g. I saw Dash Berlin here once).

2. Sound Bar:

This is also a night club that houses some DJs from time to time.

3. Three Dots and a Dash:

This is a speakeasy that has very instagram/snapchat worthy drinks. It’s worth checking out.

4. Signature Room:

If you’re not willing to pay to go up to Willis Tower, you can come here to grab a drink and get a free view of Chicago. It’s great to see both during the day and at night because of Chicago’s night lights.

5. JPark Rooftop Bar:

This is a rooftop bar that is just a great place to chill and relax. You can place reservations if you have a large group, so make sure to do that, else it can get crowded.

6. Goose Island Brewery:

Heard it’s good. I’ll have to check it out and leave my comments here sometime.

Getting Around

Before the advent of Uber/Lyft, you could definitely get around by just walking and taking the subway. There is a ‘blue line’ that is open 24/7, which is AMAZING. Chicago sells 3 day all-you-can-ride tickets for $20, but to be honest with Uber/Lyft, you can easily get around and save a lot more time.

Coming to/from the airports, you can easily take the subway lines to wherever you’re staying. I would recommend this over Uber/Lyft because it’s only a few dollars.

Once you’re downtown, generally you can walk everywhere. So I would advise just using the subway to/from the airport and then Uber/Lyft with your group elsewhere. Obviously if you’re solo traveling, I would probably get a multi-day subway pass.


  1. Q: Where should I stay?
    A: Generally, I’m an advocate of staying downtown because then everything is walking distance. If not, I would try to stay within walking distance to a subway station.

  2. Q: I only have a day in Chicago, where should I go?
    A: Purple pig, Girl on the goat, Lou Malnati’s to eat. Cloud Gate / Millennium Park and the River Walk to see. Signature Room for a night time drink if you have the time.

Images in Chicago

Here are some of my favorite photos in Chicago, taken with my favorite camera: