Chicago Unlocked: How To Plunge into the Soul of the City with Our Guide

As someone who travels to Chicago frequently, I can comfortably call myself a native now, lol. I’ve been visiting the city at least once a year since I was 11, and I love it so much. Despite my family living there, I’ve been able to experience so much that the city has to offer. Filled with a melting pot of culture and arts, Chicago is what I like to describe as a ‘chill person’s New York.’ It’s still the city, but a little less chaotic than New York. From the Cubs stadium to the glistening blue lake to the dense and amazing food scene, the city has so much to offer, and I’m excited to help you plan your perfect Chicago itinerary.

Where to Stay?

Now, I know that Chicago has a stigma behind it. The city has been named one of the most dangerous cities in the past multiple times. While I don’t want to say that there isn’t any “danger,” I do think that it’s been blown out of proportion. There are specific neighborhoods and areas that you may want to steer clear of. This typically consists of the south side of Chicago and some west side neighborhoods, such as Washington Park, Garfield Park, and more areas that you can find from this Chicago local. But, that’s not typically where the touristy places are, or close to downtown. The areas where you’ll most likely want to stay as a tourist, or even an incoming professional moving there would be the following:

• Lincoln Park – parks, beaches, great for families, near downtown
• River North – filled with restaurants and close to the loop
• Roscoe Village – more family-based
• Lakeview – nice neighborhood, well-connected with public transportation
• Loop – the heart of downtown, always bustling with many museums
• Streeterville – Magnificent Mile, Hancock building, Navy Pier
• Rogers Park – LGBTQ+ friendly, community-oriented and diverse
• Logan Square – filled with young adults

These neighborhoods all have consistent access to reliable Chicago public transportation, which will take you anywhere in the city, including to and from O’Hare International Airport! They also offer diverse food and cultural options, from Rogers Park being a very diverse and welcoming community to Lincoln Park having the zoo and access to the beach. Where you stay may help you feel safe and contribute to the vibe of your trip. If you primarily have tourist attractions on your itinerary, the Loop, River North, and Streeterville may be your vibe. But if you want a slower pace, to enjoy the environment of the city while seeing the tourist sites as well, you may want to go with Lincoln Park, Logan Square, Rogers Park, or Lakeview/Roscoe Village.

Public Transportation

Speaking of getting around, the ‘L’, the train system is incredibly efficient and reliable. You can get to any part of the city. The different color lines are helpful with the Blue line heading to O’hare, most all lines going into the loop (downtown). For any plan in your itinerary, you’ll be able to get there through public transportation!

Hungry???

Now, if you’re looking for food, you’ve traveled to the right city. Chicago is a foodie’s heaven. With so many culturally diverse restaurants and innovative restaurants along with world-renowned chefs, you’ll find something to satisfy all of your hunger needs. I had the privilege of being in Chicago last year during restaurant week in January, so I was able to try out a few popular restaurants while staying under budget. My top recommendations:

Cultural Eats:

• Demera: Great Ethiopian food and they also have a new location in the Time Out Market.
• Palace Gate Restaurant: Near Uptown with great Ghanaian food and has great spice.
• Tonys Burrito Mex: In Roscoe Village, affordable and amazing Mexican food, you also get a lot and you can tell it’s authentic.
• Tac Quick Thai: A must add to your itinerary!! Some of the best Thai food that I’ve had outside of Thailand. And the prices aren’t that bad, I would highly recommend to anyone! The drinks were also pretty strong which is a plus.

Popular Spots:

• Aba: Great for a date night or cute dinner with the girls. Family-style and everything was amazing. Located in Fulton Market, it’s also beautiful inside.
• Cindys rooftop: Great for brunch with amazing views of Millennial Park. Just make sure that you have a reservation!
• Ramen-San: Great ramen with multiple locations.
• Barrio: Located in River North.
• Machine Engineered Drinks and Dining: In Wicker Park, great location and really cool drinks.
• HoneyBear Cafe: The best French Toast I’ve ever had in Rogers Park.
• BITES Asian kitchen & bar: Near Wrigleyville.
• Elina’s: Great food and family-style. Pretty popular so make a reservation!
• Gibson’s Steakhouse: If you’re looking for something more nice and upscale, this steakhouse was amazing and has great service!

Of course, you have to get a Chicago dog while there. You can find them almost anywhere downtown. Also, while walking around downtown, my friends and I found a plaza with food trucks selling all types of assorted meals at the Daley Plaza City Market. We ended up getting the Harold’s Chicken Shack food truck along with trying our first Chicago dog!

Also!! You’ve probably seen the Cloud Bar at the John Hancock building to get a drink and see views of the city. However, tickets are $30+ just to get in…not for the drinks. We found a loophole and instead went to the Signature Room @ 95th, a bar just 1 floor below with phenomenal views. Unfortunately, they’ve permanently closed since September 2023. However, be on the lookout to see if another ‘free’ option will open in the near future that you could add to your itinerary!

Things to do!!

Now, of course, you probably didn’t just come to Chicago for food (although I wouldn’t blame you). There’s so much to see and do, and of course, you can do the touristy things such as:

• Millennium Park
• The Bean
• Navy Pier
• Magnificent Mile (Michigan Ave)
• Shedd Aquarium
• Lincoln Park Zoo (free)
• Riverwalk or Chicago Architecture river cruise
• Art Institute of Chicago
• Willis Tower Skydeck

But there’s also a lot more with much fewer people to take in the city!

• Go to a Cubs game (if in season)
• Take a Divvy bike and ride along Lakeshore
• Check out to see if there are any festivals going on.
• Especially in the summer, there are at least 3 festivals happening on the same weekend, check one out!
• Go see a show, such as the Blue Man Group
• Check out the various museums and sculptures throughout the city
• If you’re a fitness buff, download classpass and try out some classes while you’re visiting.
• During the summer, there are usually movies in the park at Millennial Park.
• During the winter, there is ice skating at Millennial park.
• During the summer, Friday Morning swim club. Take a dip in the lake.
• If you have a pup, take them down to the dog beach.
• Explore the local street art and galleries.
• If you have kiddos, there are parks all over the city. Especially in those neighborhood mentioned above that are very family-friendly. I love going to these parks with my niece and nephew so be sure to allow your kiddos to run around!
• Go shopping in Wicker Park to find more boutiques.

Add any of these to your itinerary for good times and good vibes while experience this new place!

NightLifeeee

Nightlife was pretty cool in Chicago. I think that because we were with a larger group we had such a great time! We didn’t go to main larger places, but here are some recommendations based on where we had an amazing time, and based on what we’ve heard is a pretty popular place. If you’re looking for some nighttime activities for your itinerary, be sure to add any of these places!

• Emporium – a Barcade with multiple locations. We went to the one in Fulton Market and it was pretty cool.
• Tao
• Heaven
• Federales – This place is pretty popular and they have ice shots. This is where your shot comes in a glass made of ice and after the shot you can throw your glass at a target. If you make it, your next shot is free. This is right next to Emporium so our vibes were high going in and we had a great group.
• Celeste – the DJ’s here were immaculate and so were the vibes. Great set up!
• Hangge Uppe – a dive bar and it was my first dive bar experience but it was great vibes and friendly places there.
• Brando’s Speakeasy – Karaoke bar, definitely get there early to get on the list for karaoke. It took forever to get to our song but the energy in the room was so infectious that we had a really fun time while waiting.

Other Resources

As you build your perfect Chicago itinerary, be sure to check out my travel planning blog post for some tips on how to successfully plan this trip AND how to keep it within budget!

Check out my video of my solo date that I took myself on while in the city. Regardless, Chicago is not just a city; it’s an experience waiting to unfold. From the vibrant neighborhoods to the mouthwatering culinary delights, the Windy City offers something for every kind of traveler. As a city that has been unfairly stigmatized, Chicago welcomes visitors with open arms and proves that it’s much more than its past reputation. Remember to explore beyond the well-known landmarks – ride a Divvy bike along Lakeshore, attend one of the numerous festivals happening throughout the year, or catch a Cubs game for an authentic Chicago experience.

The city’s dynamic atmosphere and friendly locals make it a destination worth revisiting, and each trip offers a chance to discover something new. So, pack your bags and get ready to embrace the perfect Chicago itinerary – a blend of iconic attractions, hidden gems, and the unmistakable spirit of this incredible metropolis. Chicago, with its unique blend of charm and urban allure, awaits your exploration.

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