When you think of the largest cities in the United States of America, what comes to mind? If you thought of either New York City, Los Angeles or Chicago, you named one of the top 3 most populated areas of the U.S. These cities are on the top of everyone’s travel list. Each location has its own character and major iconic landmarks that everyone is aware of, as well as an abundance of things to see and do. Each city has its own characteristics and unique food scene.
Before You Start Planning
Chicago experiences all four seasons, so be mindful on which type of weather you are most comfortable with. For me, great weather is when it is nice and sunny with temperatures in the 70s. However, I visited Chicago in February, which was 7 degrees Fahrenheit and snowing, the polar opposite of what I am used to.
This made my experience a little tougher to enjoy. As a Californian, I have never experienced cold like that before and I know it can get worse. Make sure to check the weather before planning your trip. You don’t want to be caught in the Snowpocalypse like I did.
How Many Days is Recommended?
All of the tourist items in Chicago are located in the Chicago Loop and can be finished within a day. The other days that you spend there can be used by being immersed in the culture and dining experience. Depending on how many restaurants you have on your list, I would say 2-4 days would be enough to experience Chicago.
There is public transit such as the trains called the ‘L’ and buses, which you can use to maneuver around the city. Having a car would be helpful but not necessary, it could also be a hassle due to parking. There are rideshare services such as Lyft and Uber, and also taxis available to take you to places outside of the city center if you do not rent a car.
For accommodations, there are many choices depending on what you are most comfortable with and where you want to stay. Hotels, Airbnbs, and hostels are spread throughout the city and can accommodate all budget types. I would suggest staying in the city near all of the food and entertainment so you can walk rather than drive or take a taxi everywhere.
On my trip, I purchased a packaged vacation for Southwest Airlines and the DoubleTree hotel located in downtown, central to everything.
Eat the Iconic Chicago Style Food: Deep Dish Pizza and Chicago-Style Hot Dog
First things first, food! The two most popular Chicago style foods are the deep dish pizza and Chicago-style hot dog. They are different than the average pizza and hot dog you have anywhere else.
You can’t go to Chicago without having a slice of a deep dish pizza. It is jam packed with cheese, not suitable for the lactose intolerant. The experience in it of itself is a food awakening. The venues are dimly lit with tables seated close together, making it an intimate dining experience. The deep dish pizza is a process to make and requires time for preparation, thus it is necessary to allocate enough time to assemble. Pizza in Chicago is a table dining experience rather than a grab-and-go like other pizza hubs across the nation.
The two main competitors of the Deep Dish pizza are Lou Malnati’s and Giordano’s. Lou Malnati’s, not to be mistaken as Illuminati, is only available throughout Chicago, whereas Giordano’s has expanded across the nation. It is often argued that Lou Malnati’s has a buttery crust whereas Giordano’s is soggy. Try both and decide for yourself which one you prefer!
The typical hot dog consists of a bun, hot dog link/sausage, ketchup, and mustard. The Chicago-style hot dog, however, comes with an all-beef Frank encased in a poppy seed bun with tomatoes, pickles, sport peppers, sweet relish, yellow mustard, and celery salt. I can eat these all day!
The Chicago-Style Hot Dog is available throughout the entire city, great for lunch, dinner or a quick snack. Some places you could get your hands on these delicious dogs are Superdawg, Gean & Jude, and Portillo’s which can be found throughout the country. The hot dog chain, Portillo’s has a ridiculous Chocolate Cake Shake that is for the fatties at heart, with a secret, unexpected ingredient… mayonnaise! There is an abundance of hot dog stands and shops that you can even do a Chicago-style hot dog crawl to deem which hot dog trumps the rest.
Don’t leave Chicago without trying these food items!
Shuffle and Fist Pump to House Music
“I must of went to house heaven… because nothing is that divine” – Divine by Jamie Antonelli
The birth of Chicago House, or simplified to House music, was right in the city of Chicago after the disco era. This gave rise to the nightlife and changed the sounds of dance music.
Nightlife in Chicago is similar to the nightlife in large cities like Los Angeles. There are clubs throughout the city where they let you in free of charge, all you need is their secret “password”. These are similar to being on the “guest list” in other parts of the country.
During my time in Chicago, I went to The Mid, which has the atmosphere of a warehouse party and Sound Bar. Unfortunately, I got wind that The Mid closed its doors in 2019. There are clubs and bars that still have their doors opened such as Stereo Nightclub.
South of the Chicago River, the Chicago Loop is where most tourists flock.
With Chicago not having many places to sightsee for tourists, Millennium Park has been the center of tourist attractions. There are several art displays and statues you can stare at and try to make sense of what it is supposed to be.
Other than the Deep Dish Pizza, Chicago’s most iconic landmark, referred to as “The Bean”, is Cloud Gate. It is an art sculpture that turned into the most visited spot in the city. When you look in it or take a picture of it, it reflects the beautiful Chicago skyline of tall buildings. Go under it and take a look at your warped reflections.
During the winter season, a section of the park is turned into an ice skate rink. You can truly get into the spirit of the season by gliding around in the natural cold weather. Admission is free and open to the public. If you don’t have any ice skates, you can rent them on the spot for $13-15.
A very silly fountain located in the vicinity of Millennium Park. It is an art display consisting of LED screens with the illusion of different people spewing water out of their mouths.
“Love and marriage, love and marriage. Go together like a horse and carriage.” Does this theme song sound familiar? It should! But for those unfamiliar, it is from the television show, Married with Children.
Not to be confused with the Buckingham Palace, Buckingham Fountain is one of the largest fountains in the world and has a cameo in the Married with Children title sequence. Just a stone’s throw away from Millenium Park (about a half mile walk), is another great opportunity to take another one of Chicago’s treasured architecture.
Willis Tower (Skydeck Chicago)
Formerly known as the Sears Tower. If you ask any of the locals, they will point you to visit this. The Skydeck is most famous for the “The Ledge” where you can take photos of yourself sitting or standing on top of a glass that overlooks the city.
To get here, you must buy admission tickets to go up the elevator that takes you to the 103rd floor. Once you get there, it is free to sit on top of the glass and take a photo. Worth a visit since the views are spectacular!
Similar to many piers across the United States, Navy Pier is your typical pier with your average Ferris wheels, rides, and entertainment. However, it is on a much larger scale than Santa Monica Pier and the like. The Navy Pier also holds restaurants and the movie theaters. It is also large enough to host concerts and events.
During my time in Chicago, I was able to purchase last minute tickets to see Above and Beyond, well-known Trance duo.
Chicago is divided into 2 parts, North and South. The Chicago River is the body of water that divides the city. During the winter, the river is frozen and walking by it will make the wind feel like ice daggers.
For all of your shopping and fashion needs is the Magnificent Mile, just north of the Chicago River.
John Hancock Tower (360 Chicago)
In lieu of the Willis Tower, you can view the city from the observation deck of the John Hancock Tower called 360Chicago. It is a shorter wait time and cheaper admission prices. For an extra cost, you can experience Chicago with a thrilling “ride”, TILT. This experience will tilt your body outward so you are at a 30 degree lean above the city. The only thing preventing you from falling is a glass window and the metal bars you hang onto on the side.
There is also a way around paying for the observation deck if you just go to the Signature Lounge on the 96th floor to grab a drink or dinner. Please be advised that the prices are a bit pricier due to the location and the cost of the view.
Chicago Water Tower
Located in the Magnificent Mile neighborhood, the Chicago Water Tower is an interesting stop. This historical architecture is best viewed in the day time to capture its style and elegance. On the outside, it will probably take you a good 5 minutes to look at it and take a picture of. It is no longer used as an actual water tower but rather as a gallery to hold the photographs of the Water Tower.
Joe’s Seafood, Prime Steak & Stone Crab
Located in Magnificent Mile, Joe’s Seafood is one of the highest rated restaurants, where you can get surf and turf dinners. As stated in their name, they are known for their stone crabs. It is an upscale, fancy restaurant so don’t come in wearing shorts and sandals.
My experience was that it was nothing different from other steakhouses, it is similar to Ruth’s Chris and the like. It wasn’t until afterward that I realized that Joe’s Seafood has restaurants located in Las Vegas, and Washington D.C. as well. If you frequent Las Vegas and Washington D.C., I would save Joe’s Seafood for those cities and explore another restaurant only available in Chicago.
Devon Seafood Grill
Upscale seafood restaurant with an amazing happy hour! The oysters are only $1 and the fresh appetizers such as calamari are at very reasonable prices.
The Purple Pig
All pig dishes. All pig parts.
If you love eating pig, this is your place! If you don’t, like me, you will have trouble finding things to eat. They have all of the pig parts you can think of: pig ear, pig head, pig liver, etc. This is a tapas style restaurant where you should order multiple dishes and share them amongst your party.
We didn’t have any reservations before entering but was able to be accommodated. But as always, if possible, make reservations beforehand!
When you dim the lights to restaurants, that’s when you know they are fancy right? Bavette’s has the dimly lit, fancy restaurant feel. Not only that, the atmosphere and ambiance take you back to the old school, Chicago mob-life days. Bavette’s is designed as if you are in a speakeasy during the Prohibition era.
It is known as a steakhouse with all of its usual fixings such as steak, seafood and crab cakes paired with aesthetic cocktails you can enjoy. Bavette’s is one of the highest rated restaurants in Chicago and has recently opened another location in Las Vegas.
An Italian marketplace where you can find Italian food and drinks. Eataly has your favorite Italian dishes such as pizza and pasta. And yes, there’s gelato! You can find a majority of your favorite Italian products here, whether you want to eat it in house or take it home to cook yourself. There are several locations available throughout the nation as well as worldwide. Nestled in large cities, Chicago is 1 of 5 locations in the U.S.
Five Faces Ice Cream Shop
To my disappointment, this place is not an actual ice cream shop. Five Faces Ice Cream Shop made up my disappointment by offering some of the best late night snacks. You can get a Chicago-style hot dog or some chili to help warm up the cold weather. The employees there are friendly and will joke around with you despite having to work graveyard shifts.
Fulton Market District
The Fulton Market District is another gentrification story added to the history of the city of Chicago. When you are here, it is evident of what it used to be, meatpacking, industrial district. You will get a sense of the old and the new coming together to make it a more modern area filled with trendy restaurants such as Girl & The Goat, Little Goat Diner, Duck Duck Goat, and Au Cheval. It is rumored that the double cheeseburger at Au Cheval is something to rave about. But let me know if you think it is overhyped. As an added bonus, check out the Mcdonald’s new headquarters in this area!
Grab breakfast or brunch at The Publican. It is one of the modern restaurants located in the Fulton Market District with community style seating — meaning one very long table with seats facing each other. I had brunch here and personally it felt a little overpriced for what you get and our toast was burnt.
Make sure to grab reservations if you can as it gets extremely crowded during the mornings.
Home of the Chicago Bulls and the Chicago Blackhawks. Perfect for if you are a basketball or hockey fan. If there isn’t a game happening, you can still visit the United Center and pose with the statue of the apparent “best basketball player in history”, Michael Jordan. Also, you can see other statues of legends in hockey.
The Fun Doesn’t Stop Here
- Dine at the Michelin-starred Alinea, a most well-known restaurant and sought after seat in Chicago
- Grab a late night snack at Jim’s Original, great hot dogs for when you have the drunchies. Not a Chicago-style hot dog spot, but a hot dog nonetheless.
Bonus: All sandwiches come with fries!
- Fan of the show “Shameless”? The Gallagher’s house is located in Lawndale, Chicago but it is in the bad area of town so if you truly need to visit, take your picture and GO! Do not linger around.
- Get happy hour oysters at Shaw’s Crab House