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When I decided to plan a trip to find the best things to do in Chicago, I saw it as an opportunity to do something I had never done before. Normally one to Google, plan, research, and then Google some more, I challenged myself to not look up anything and instead, strictly take the advice of the locals. Did it pay off? Absolutely.

10/10 recommend an architecture cruise

The first time I *technically* set foot in Chicago was in 2019 after missing my layover flight from LA to home. It was late, I was tired, and I knew nothing about the city (other than it was supposedly “windy”). I didn’t even have a hotel booked. I don’t know if it was luck or fate, but when I got into the cab and told the driver to “take me somewhere downtown,” my entire perception changed. The hotel that I stumbled upon ended up being across from the Chicago Theatre, and one look at the city skyline reflecting off the Chicago River told me this would not be my last time here. Fast forward to now, and the approach I took to exploring the city was to ask those who knew it best. This blog post contains the best things to do in Chicago, all of which were recommended to me by locals <3.

HUGEEEE s/o and thank you to Hiedy, Erin, Aubrey, Sulah, Katie, Samantha, Nikki, and all the kind, random strangers that crossed my path and made this blog post possible. Y’all really made a small-town girl feel welcome <3

Chicago at night

Website Disclaimer: I first visited Chicago in August 2022. Although everything is accurate as of the publication of this post, it is important to keep in mind that prices, attractions, and other things may change with time.

**September 2022 update features the following bars/restaurants: Avli, Lil’ Ba-Ba-Reeba, TAO Chicago, The Godfrey Rooftop, and sports bars

Best Things to do in Chicago: Table of Contents

The Food
The Bars
The Shopping
The Neighborhoods
Activities & More

The front of the entrance to Millennium Park
Exploring Millennium Park

Best Things to do in Chicago: The Food


Goddess and the Baker – Coffee shop ($$$$)

  • Location: Multiple
  • I liked this place so much I went here multiple times. My go-to is their Mayan mocha with oat milk, along with the smoked salmon bagel. They have a massive dessert case filled with cookies, croissants, cupcakes, etc. that I could spend all day fantasizing over. Try one. Try them all. I’m obsessed.
Goddess and the Baker

Eggy’s Diner – Breakfast/Lunch ($$$$)

  • Location: Multiple
  • This one is more of a comfort food vibe. I ordered the crab cake eggs Benedict because, well, #eggs. When it came out, the crab cakes were fried. If this is your vibe, you would love it. It was not mine. If I had to go here again, I would do the pancakes or waffles.

Travelle’s at the Langham – Breakfast/Brunch/Lunch/Dinner ($$$$)

  • Location: The Loop
  • Restaurant inside the Langham hotel with a gorgeous interior and an equally impressive menu. I’m still not over the floor-to-ceiling windows.
Travelle’s at the Langham

Beatrix – Breakfast/Brunch/Lunch/Dinner ($$$$)

  • Location: River North, West Loop
  • Again, another place I liked so much I went multiple times. I tried something new each visit and am convinced the kitchen staff can do no wrong.

Mi Tocaya – Dinner ($$$$)

  • Location: Logan Square
  • This place is out of the way if you are staying in the city but so worth it. I got the chicken tacos (Taco(s) Arabe de Pollo), chips & guac, and a spicy marg.

The Cherry Circle Room at the Chicago Athletic Association – Breakfast/Lunch/Dinner ($$$$)

  • Location: The Loop
  • This is not the first time I will mention the Chicago Athletic Association on this page. The Cherry Room has the perfect ambiance of expensive-library-meets-speakeasy-dining-lounge. You can study, you can eat, you can write a blog post (which is actually what I am doing now!)
The Cherry Room at Chicago Athletic Association

The Hampton Social – Brunch/Lunch/Dinner ($$$$)

  • Location: River North, Streeterville
  • Great food, staff, ambiance, everything. I tried the Ocean Eyes cocktail and the tuna tartare and loved both

Big Star – Lunch/Dinner ($$$$)

  • Location: Wicker Park
  • Mexican joint with outside seating, rustic atmosphere and amazing marg’s

Lil’ Ba-Ba-Reeba – Brunch/Lunch/Dinner ($$$$)

  • Location: River North
  • Rustic-chic Spanish restaurant serving tapas (and we all know how I feel about Spain! ❤️). Shoutout to Eslam for the best margs and espresso martini (and not trying to stop me when I went from tequila to vodka).
Lil’ Ba-Ba-Reeba

Avli – Brunch/Lunch/Dinner ($$$$)

  • Location: Multiple
  • Contemporary Greek restaurant with incredible food/atmosphere. Their website lists fun upcoming events and even has a tip-sheet section for those actually traveling to Greece in the future.

TAO Chicago – Dinner/Nightclub ($$$$)

  • Location: River North
  • Where do I even begin? The food, the atmosphere, the music, the service…literally EVERYTHING about this place is mind-blowing. Perfect for a celebratory date night or meeting your friends for a bougie girls-night-out.
    • FYI – TAO also has locations in NYC, Las Vegas, and Los Angeles
Reunited at TAO with my favorite Chicago ladies!
TAO Chicago restaurant interior

Lou Manalti’s vs. Giordano’s – Deep Dish Pizza ($$$$)

  • Location: Multiple
  • Perhaps the only Chicago rivalry bigger than Cubs vs. White Sox is Lou’s vs. Giordano’s. I had way more people tell me Lou’s was better, and so that’s the one I chose to try out….
    • My honest opinion? It was just okay. If you’re from Chicago, you probably hate me (unless you’re #TeamGiordano). I’m sorry. It was the crust. I like a more doughy pizza crust. Now you REALLY hate me, don’t you.

Eat Your Way Through the West Loop

  • Notable streets: Randolph St., Fulton St.
  • West Loop is arguably the best neighborhood for foodies in all of Chicago. You will find a ton of award-winning restaurants ran by Top Chef winners, and others claim Michelin Star accolades. Walking down Randolph or Fulton St. boasts a quaint, atmospheric vibe with string lights, greenery, and lots of outdoor seating. Nobody gave me any certain recommendations here, and instead told me “you can’t go wrong.” So that’s what I’m telling you too.

Because We All Love a Good Food Pic:

Best Things to do in Chicago: The Bars

Sit-Down Bars, Rooftops, and Live Music

The London House Rooftop – for the best views

  • Location: The Loop
    • Voted the #2 rooftop bar in the country, the LH Rooftop boasts incredible views of the city. I recommend their spicy marg if it is on the menu!
The view of downtown Chicago from the London House rooftop bar
View from LH Rooftop

The Gage – for a chill night

  • Location: The Loop
    • I was told by a local that the drinks are good but the food is “eh.” I tried their spicy marg here (I know, I have a type don’t I…), but was not overly impressed. I was told to get the imperial whiskey punch if it was on the menu, but it wasn’t. If I came back, I would try this.

The Bassment – for live music

  • Location: River North
  • This place is insanely fun – they have live music and sing everything from Motown to Snoop Dogg to Notorious B.I.G.
  • You can check in advance to see who’s performing. All the performers are incredibly talented, but my personal favorite is when Angela Martin & Que Billah are on stage.
  • Thank you Sulah/Erin/Aubrey for suggesting this place! I loved it 🙂

The Robey – for (more) amazing views

  • Location: Wicker Park/Bucktown
  • If you’re familiar with NYC, this place reminds me of the Flatiron building. As the only skyscraper in this section of town, the Robey is definitely a standout. It’s a great place to grab a drink and soak in the views from a different side of the city.

Cindy’s at the Chicago Athletic Association

  • Location: The Loop
  • I went here during my last night in the city and actually ended up getting food AND drinks. The atmosphere was beautiful and the service was top notch. The waiter recommended the Tierra Roja, assuring me the passion fruit would tone down the smokiness of the mezcal (I’m more of a blanco girl). He was right. I have zero regrets.

The J. Parker

  • Location: Lincoln Park
  • This rooftop bar/lounge sits atop the Hotel Lincoln and is perfect for those who want a night out away from the city center. You still get amazing views of Chicago’s skyline and Lake Michigan. Their signature cocktails are insane in the best way, and they also have a small food menu.

The Godfrey Rooftop

  • Location: River North
  • The views. The drinks. The aesthetics. This rooftop bar has one of the best panoramic views of the city (see photo below, although IMO, the photo doesn’t do it justice).

Sports Bars

Full confession: I love a good sports bar. My favorite thing to do in the fall is find a place with good food & beer and watch college/NFL football. You probably thought I was going to say walking down the street with a PSL and Ugg boots. I know, I’m full of surprises 😉.

Old Crow Smokehouse ($$$$)

  • Location: Wrigleyville
  • This one was my favorite out of all the sports bars I went to. You can sit inside or out, there’s a ton of TVs, and they have a great food/beer menu. Oh – and it’s essentially steps away from Wrigley Field.
Old Crow Smokehouse in Wrigleyville

Jake Melnick’s Corner Tap ($$$$)

  • Location: River North/Streeterville
  • Their website boasts “best wings in Chicago” and I would have to agree.
    • They serve both boneless and bone-in wings & IMO, the bone-in wings are better.

Bub City ($$$$)

  • Location: River North
  • BBQ place with a Texas-style atmosphere that includes string lights, plenty of TVs, and an extensive drink menu (beer, cocktails, seltzers, and even wine). Their whiskey selection is super impressive.
  • They also have live, late-night country music, usually starting at 10pm.
Bub City whiskey bar
Bub City

Theory ($$$$)

  • Location: River North
  • Part sports bar, part lounge (although I only witnessed the sports bar). This bar was my 2nd favorite due to the amount of TVs and the food menu. They also serve a variety of alcohol (beer/cocktails/seltzers/wine).
    • My ONLY complaint: the beer was served in plastic cups. It was late in the afternoon, so I’m giving them the benefit of the doubt and saying all their glasses were dirty….

Best Things to do in Chicago: The Shopping

The Magnificent Mile

The Magnificent Mile is Chicago’s most famous shopping district. It has everything from Forever 21 to Louis Vuitton. Some key places to note include:

The Shops at Water Tower Place

  • This was my favorite indoor shopping plaza, solely because of the variety of stores and restaurants. Check out their Directory for more info.
    • My favorite store in Water Tower was Free People. I am a FP fan at baseline, but this store exceeded my expectations with the cute stuff they had in stock and how helpful their employees were. (Hiedy has the most amazing style – I would let her dress me any day of the week!)

Nordstrom on Michigan Ave.

  • This Nordstrom is the largest in the country and has 4 levels. It is located in a shopping center, and the rest of the stores are significantly less impressive IMO. However, going to this Nordstrom is worth it. There is a Louis Vuitton inside, and their selection of clothes and shoes is enough to keep you entertained for hours.

The Shops at North Bridge

  • Similar to Water Tower, North Bridge has a variety of stores (although less popular). There’s another Nordstrom here as well, in addition to a variety of restaurants.

900 North Michigan Shops

  • This shopping center boasts 7 levels of high-end retailers, restaurants, and even a Top Golf Swing Suite.

Boutique Shops

A lot of really cute boutiques are located near the northern neighborhoods in Chicago. I spent a lot of my time walking down the streets of Wicker Park, Bucktown, and Lincoln Park and checking out the locally owned stores. Some notable ones include:

  • Mulberry & Me – Wicker Park (my favorite boutique!)
  • Gemini – Wicker Park (hipster vibes)
  • Penelope’s – Wicker Park (hipster vibes)
  • Door 24 Wine – Bucktown (this is actually a wine shop, but I’m throwing it in here because they have free wine tastings on Fridays from 5:30-7:30…I know, right??)
  • P45 – Wicker Park/Bucktown (upscale)
  • Scotch & Soda – Wicker Park/Bucktown (casual-chic)
  • Art Effect – Lincoln Park (clothes, art, gifts – I LOVED this one!)
  • Bliss & Belle Boutique – Lincoln Park (casual-chic)
  • Alice & Wonder – Lincoln Park (casual-chic)
The entrance to Door 24 wine shop in Chicago, Illinois
Door 24 Wine

Best Things to Explore in Chicago: The Neighborhoods

Lincoln Park

In the words of one of the locals, “Chicago is all about its neighborhoods.” The areas outside of the city are less touristy and give a more suburban, quaint feel that is a contrast to the tall skyscrapers and bright lights. Some that I would recommend checking out include:

  • The Loop/River North – the main hub of the city. This is where you will find the River Walk, skyscrapers, Millennium Park, tons of restaurants and bars, the Chicago Theater, and more.
    • Notable streets include Michigan Ave, State St, Randolph St, and Wabash St.
    • This area is designed like a grid, making it very easy to navigate (and if I’m saying that, you know it’s easy).
  • Wicker Park/Bucktown – good for boutique shopping; very artsy. IMO, this area was serving Brooklyn vibes in the best way.
    • Main streets include N. Damen Ave, Milwaukee Ave, and W. Division St.
    • The intersection known as “6 corners” is a busy area that is home to a lot of shops including boutiques, vintage stores, hipster cafes, and more
  • Gold Coast/Streeterville – very ritzy area right near the Magnificent Mile.
  • Lincoln Park – similar to Wicker and Bucktown in the sense of artsy and trendy
    • Notable streets include Fullerton Ave (for architecture) and Armitage Ave (for shopping)
  • Lincoln Square – known for its German roots, this neighborhood has plenty of German restaurants and bars, along with Bavarian-style bakeries.
  • West Loop – good for restaurants, as mentioned above.
    • Notable streets for the best restaurants include Fulton St and Randolph St.
  • Printer’s Alley
    • Check out Sandmeyer’s Bookstore, Printer’s Row Wine Shop, and all the restaurants on Dearborn St.

Best Things to do in Chicago: Activities and More

  • Take an Architecture Cruise – this was my FAVORITE THING I did all week (besides eat). You can take a cruise in the daytime or at night as the sun is setting. Add this to your Chicago must-do list!
    • I booked my cruise through Get Your Guide with Wendella Tours and did the 8:30pm time slot. Seeing the city all lit up from the tour boat is a memory that will forever live in my head rent-free. It was indescribably beautiful. My tour guide was knowledgable, funny, and had a genuine love for Chicago that was evident through her storytelling.
    • They also stop the boat every so often so you can take photos.
  • Navy Pier – ride the ferris wheel, which was actually invented in Chicago!
  • Go to a festival – Chicago has TONS of festivals throughout the year, and you can Google to see which ones are taking place on what days. (I missed the Sangria Festival by one week….sighhhh.)
  • Do a river walk – listen, once you visit, you’ll understand why I’m obsessed with the river. There are restaurants and live music, and it’s a great place to meet people.
  • Explore the city streets – with a never-ending abundance of restaurants, bars, shops, and more, you’ll always find something new.
  • Check out the iconic Chicago Theatre – you can catch a show here, do theater tours, and more
  • Do a tour – Chicago has a variety of crime tours, museums, and more that are all worth exploring.
  • Visit Millennium Park and get a photo by the famous Cloud Gate statue, aka “The Bean.”
  • Visit Skydeck Chicago at the Willis Tower and get a photo on the Ledge, a glass box that extends out 4.3 feet from the building and gives you unparalleled views of the city.
  • MusicBox Theatre on Southport Ave – historic theater featuring independent, current, classic, and cult films. They also have late night patio screenings if you’re a night owl, plus a lounge & garden section offering beer, wine, and cocktails.
  • Walk up Prairie Ave, aka Millionaire’s Row, and check out the mansions belonging to Chicago’s elites

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