A Weekend Guide to Chicago
- Lauren
- 1 day ago
- 7 min read
It's so surprising that it took me over twenty years to visit Chicago since it's only a 2.5-3 hour flight from Texas! I finally made it to one of the largest and most popular cities in the USA. Luckily, I had an experienced Chicagoan accompanying me on my journy around the city to have the best possible experience.
As a city that dates back to the 1700s and was home to the Chicago World's Fair and world's first skyscraper, Chicago is FULL of history! "The Windy City" also boasts some of the USA's best museums, theaters, and festivals. With a range of activities, Chi-town is a great city to visit for people of all ages. Need I say more?
Here is my weekend guide to Chicago, Illinois:
Where to Stay in Chicago:
Hotel
Palmer House is a great, central hotel to stay at with a lot of history! The original Palmer House Hotel opened in 1871 by Potter Palmer and, unfortunately, burned in the Great Chicago Fire. The hotel was rebuilt in 1873, with decor inspired by his wife's French heritage and friend, Claude Monet. The hotel is also where the brownie was invented. A pastry chef created the popular dessert, as requested by Palmer's wife, to present and serve at the Chicago World's Fair. Although the hotel is now part of the Hilton hotel group, Palmer House is still considered the longest continually operating hotel in the United States.
The hotel is extremely central, with Millennium Park (The Bean!!), Art Institute of Chicago, restaurants, and more at your fingertips!
What to Do in Chicago:
Located in Grant Park, the Art Institue of Chicago is one of the USA's largest and oldest art museums! The museum itself was founded in 1879 and the building that houses the museum was built for the Chicago World's Fair. This museum has over 300,000 pieces of art in its permanent collection, some of which are world-renowned works of art, and it rotates through more than 30 different exhibits yearly.
Grant & Millennium Park
I'm a big fan of parks, so obviously I had to include Grant & Millennium Parks on this guide. Grant Park's 312 acres are home to the Museum Campus, Buckingham Fountain, Art Institute of Chicago, and more. The park, which was established in 1844, has also hosted some famous world events and popular festivals. It's the perfect place for a morning stroll or evening picnic, with views of downtown and the lake. Millennium Park, which is connected to Grant Park, is where Cloud Gate (aka "The Bean") and Crown Fountain are housed. The Bean is a popular sculpture that reflects the beautiful skyline and selfie-taking visitors with its mirror material. Nearby the modern-looking sculpture you can find kids playing in Crown Fountain, where water seeps from the ground and tall faces spit water out.
Riverwalk
As a native Texan, the Chicago Riverwalk made me feel somewhat like I was walking back in San Antonio, minus the Mexican Restaurants and large trees covering the pathway 😅 The Chicago Riverwalk is a great place to stroll along the river lined by restaurants and bars. In the evening you'll find boats full of passengers touring the city and at night you'll feel the magic of downtown lights. The Riverwalk is fairly close to Millennium Park, making it perfect for a dinner spot after a day in the park.
Shedd Aquarium will send you back to your childhood. Built from 1927-1930, Shedd Aquarium is the third largest aquarium in the United States. Not only does the Shedd house some of the coolest marine animals in the world, it also offers visitors the opportunity to touch some animals and see some animals show off their skills!
Lincoln Park Zoo, founded in 1868 and considered the second oldest zoo in the U.S., is located just north of downtown Chicago and is one of the few remaining zoos in the USA with free admission. Although only 35 acres, Lincoln Park Zoo houses over 200 different species of animals! The zoo is also open 365 days a year, making it perfect for visitors at any time of year.
Architecture Tour
As a city with deep history and popularity, Chicago has incredible and significant architecture. A great way to see the highlights of Chicago architecture is on a architecture tour. Here is an architecture boat tour that passes by highlights, like Wrigley Building, Centennial Fountain, and Lyric Opera of Chicago. You'll have the opportunity to learn about Chicago history and see the city from a different perspective: the river.
Festivals
The Windy City is home to some of the world's best and largest festivals! As a music festival lover, I figured I should first mention Lollapalooza. Lollapalooza is a four day music festival in the heart of Chicago with some of the most popular musicians! If you're a music lover, this is the festival for you!
Another large festival is Taste of Chicago, the world's largest food festival and Chicago's largest festival! The festival takes place over three days and boasts over 50 food vendors and dozens of musicians.
It's not necessarily a festival, but the St. Patrick's Day Parade is also a popular parade hosted in the city that features Irish dancers and a pipe band! There are so many other festivals and events around Chicago, including Open House Chicago, World Music Festival Chicago, and the Chicago Air and Water Festival.
Baseball Game
The Windy City is home to two professional baseball teams, the Chicago Cubs and the Chicago White Sox. Chicago's baseball history goes way back to the founding of the Cubs in 1870 and the founding of the White Sox in 1900. The Chicago Cubs also play at the second oldest MLB stadium in the United States! Go watch a game and grab a Chicago-style hot dog while you're at it!
See a Show
As one of the largest cities in America, Chicago hosts some of the most popular Broadway shows and incredible comedy shows. There are over 250 theatres throughout the city, five of which are Tony Award-winning theatre companies. With the abundance of theaters and different shows, there is always something to see for all interests.
A great spot of families, Navy pier consists of 50 acres of restaurants, rides, performances, and fun! The historic pier originally opened in 1916 and served different purposes over the years. It wasn't until 1995 that the pier was redesigned and used as an attraction for visitors of all ages. The pier is free and open year round. I highly recommend riding Centennial Wheel to take in the views of Chicago. For an even more special experience, ride Centennial Wheel in the summer while the Saturday night fireworks are lighting up the sky.
How to Get Around:
Walk
If you're staying and exploring in downtown Chicago, you can easily walk everywhere. A lot of attractions are within walking distance of each other and you are able to quickly stop by small attractions when walking between the larger attractions. If you would like to explore other neighborhoods outside downtown, I'd recommend using a different form of transportation.
Chicago Transit Authority is the second largest public transportation system in the United States, consisting of eight different train lines within the city and 127 bus routes. Often referred to as the "L", CTA has elevated, subway, and street-level trains. It's super easy and inexpensive to use. Two lines, the blue line and the red line, also operate 24/7. You can use the Ventra app or Ventra machines at one of the 145 rail stations to purchase tickets.
Driving
I am a big fan of driving, so I will not deter you from driving around Chicago. You can do everything on your own time and explore other neighborhoods or suburbs of Chicago if you drive. I will say, like every large city, driving around Chicago is not the easiest because of traffic and the business of downtown. Parking is also not ideal as you will likely pay more than you would like in garages in downtown. Just be prepared for potential traffic and high parking rates in the city.
Metra is the commuter train that takes passengers from Chicago to suburbs and vice versa. There are eleven Metra routes and over 200 stations. This is a great, inexpensive way to explore neighboring towns without driving out of the city. You are able to purchase Metra tickets in the Ventra app.
As someone who lives in Austin and sees people using scooters and bike shares every day, I felt a little bit like I was at home when I found out that Chicago has their own bike and scooter share program called Divvy. Chicago has plenty of bike lanes and trails for bike or scooter riders to use at any time of day. You will most definitely see Divvy stations all over the city.
Where to Eat:
Fairgrounds is the perfect spot for a coffee or tea to-go as it has an array of options and it's located in center of the city! They also have an outdoor patio area if you'd rather sit outside and people watch while you slowly sip your cup of joe.
Palmer House Hotel
I mentioned this earlier, but the Palmer House Hotel is the birthplace of the brownie. You have to eat a brownie in its birthplace, right? 🤪
We stopped at Miller's Pub for a late night snack, ordering Wisconsin fried cheese curds and an ice cream sandwich, and ended up loving it. The vibes were fun and the food was good. From the menu, we learned that the pub has been family-owned and operated since 1935!
Eggy's is a great little breakfast diner tucked away on a peaceful side street in between parks and the Chicago River. They have so many different breakfast options, from skillets and omelets to pancakes and crepes. We ate the American skillet, Eggy's crepes, and a pancake. Everything was delicious!
This is a controversial choice for Chicagoans as there are mulitple different deep dish pizza restaurants and everyone has their own opinions of each. I am not much of a deep dish pizza person but I enjoyed Giordano's. They have several locations across the city and we were able to place our pizza order while we waited for our table. I highly recommend either arriving early or making reservations for any popular deep dish pizza restaurant that you eat at. It's obviously a super popular dish to eat in The Windy City and the restaurants get busy quickly!
A trip to Chicago is not complete without a visit to a dive bar for a Chicago Handshake, a traditional drink consisting of a shot of Malört followed by an Old Style beer. Rossi's is a cool, cash only dive bar to stop at for a late night Chicago Handshake.
Whether it's your first time in The Windy city or you've visited before, there is always something to do in Chicago! Let me know which spots were your favorite and anything else that you discovered!
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