A Local’s Guide to Visiting and Understanding Chicago

view from the London House
The view from the London House rooftop bar

It’s about time I write a Chicago guide, right?! I only lived there for 8 years. This Local’s Guide to Chicago is going to have to make up for the fact that I lived in the city for so long without writing about it.

Here we go!

If you didn’t know, I recently moved to Montana! Read more about that here.

A Guide to Chicago History

Chicago, or as I’ve deemed it, the heart of the Midwest was founded in 1830 and promptly burned down in 1871. You’ve probably heard of the Great Chicago Fire – the fire that burnt at least a third of the city down. Legend has it, Mrs. O’Leary’s cow kicked a lantern which started the fire – something we all learned in school growing up. The truth is, we don’t know what started the fire, but the conditions were perfect for it. There was a drought, high winds, and a ton of wooden buildings which is a sketchy combination.

Don’t worry though – Chicago got right back up on its feet! It was nearly fully rebuilt before the 1900s. In fact, the first skyscraper EVER was built in Chicago in 1885.

For the last 100+ years, Chicago has been home to many kinds of activists. Back in the late 1800s/early 1900s, protests prevailed to protect labor workers. More recently, protests have shifted gears toward racial injustices. This has to be one of my favorite things about Chicago – the community and camaraderie found when people are coming together to fight these injustices.

Chicago isn’t all about protests, though. It’s also home to its own version of blues and jazz music, deep dish pizza, and the Chicago Cubs.

One more thing I have to include in this Chicago guide – I know it’s windy, but that’s not why it’s called the windy city! It was nicknamed the “Windy City” because of its corrupt and shifty politicians.

How to Get To Chicago

Via Airplane

Chicago has one of the largest airport hubs in the United States: O’Hare International (ORD for short). Another fun fact: ORD stands for Orchard because there used to be an apple orchard where the airport currently sits!

Anyway, you can likely catch a direct flight to O’Hare from anywhere in the US. There’s a good chance you can even find direct flights from larger cities internationally as well.

O’Hare is just north of the city and there’s also a smaller airport south of the city called Midway (MDW). Midway is MUCH less busy than O’Hare and sometimes easier to get in and out of, but the flights are much more limited here.

Whether you’re flying into O’Hare or Midway, you can take the L subway into the city. You can also opt for a cab or Uber as an alternative.

Be warned that during rush hour, it might take about 60-90 minutes to get into the city from O’Hare, resulting in a $70-80 cab ride. Uber is usually cheaper and can be anywhere from $30-50 one way.

Via Metra Train

Chicago has an awesome public transportation system compared to other cities I’ve been to. There are 3 train systems you should be aware of. The first is the L. This is the subway that will take you all around the city and spans all the way from O’hare to Midway.

The second is the Metra. This is a train system you’d use if you’re coming to Chicago from a suburb. The Metra spans a much greater distance than the L and has a few train stations in the city. The most popular for coming into the city are Union Station and Ogilvie.

The Metra comes in (or out) from as far north as Kenosha, WI, as far west as Harvard, IL, and as far south as Manhattan, IL.

See here for a full map of the Metra Train routes.

Via Amtrack Train

The Amtrack is the third train system and the largest train system in Chicago because it spans the entire United States! There are stations all across the US and even into Canada – click here for a map of all the Amtrack train routes.

If you come to Chicago via Amtrack, you’ll get off at Union Station which is conveniently located right downtown.

Via Bus

Like I said before, Chicago is the heart of the Midwest. This means you can get to the city almost any way you’d like. There is a Greyhound bus station located relatively close to Union Station downtown.

Like Amtrack, Greyhound has stations all across the US and into parts of Canada. Here is a map of the routes they offer.

Via Car

If you live relatively close to the city, it is definitely an option to drive. There are a couple major highways coming into Chicago including I-90, I-94, and I-294.

Fair warning – traffic can get insane and parking can get even worse. If you’re going to be sticking to the downtown area, I’d highly recommend using public transportation, instead.

Chicago skyline
Skyline view from Adler Planetarium

A Guide to Chicago Neighborhoods

Chicago is made up of a TON of neighborhoods, so I’m not going to go into them all in this Chicago guide, but I’ll touch on the ones you might want to visit if you’re touring the city.

The Loop

The Loop is in the center of the city and are where most of the tallest skyscrapers are. This area is mostly filled with businesses and is bustling during the week. However, on the weekends, it can get pretty quiet. A lot of the restaurants are only open Monday through Friday because they cater to the 9-5 workforce.

The only reason you’ll likely come to this area is to visit the Sears Tower (aka, Willis Tower). This is the tallest building in Chicago and you can even walk out onto a glass floor to see the whole city below you.

The Loop is also the “zero” point of the city. It’s literally where the addresses change from North to South and from East to West. It’s also the point where most people differentiate the “northern part” of the city from the “southern part.”

West Loop

The West Loop was my home for 6 of the 8 years I lived in Chicago. It’s home to University of Illinois at Chicago, Greek Town, and a TON of great restaurants.

There are some world-famous restaurants in Chicago and the West Loop houses several of them including Duck Duck Goat, Aba, and more. You can actually find a pretty good range of prices and atmosphere in this area – everything from fancy nights out to greek diners.

Other than food, the West Loop is great for casual night life. It’s demographic is mostly college students and young adults.

As a disclaimer, I personally lump Little Italy and Greektown into the West Loop. There’s some ambiguity there, but in case any of this is confusing, here’s a map of the “official” neighborhoods.

South Loop

The South Loop was my home from the other 2 years that I wasn’t in the West Loop. South Loop has definitely been growing the past few years and is getting just as popular as West Loop.

Most of this area is either residential buildings, restaurants, or bars. So, if you’re visiting for a short time, you might not make your way to this neighborhood, but they do have some great restaurants, so if you’re in town for a big longer, I highly recommend venturing to the Firehouse Restaurant for fine dining or Kroll’s for something more casual.

That said, just East of South Loop is the Adler Planetarium and Shedd Aquarium which you’ll want to visit!

River North

River North is just North of the Loop and is great for nightlife, fancy dinners, and bougie brunches. That’s about it.

Gold Coast

If you’re looking to do some heavy shopping in Chicago, the Gold Coast is for you! Gold Coast runs right along the Mag Mile along with several other luxury shops. This area is also right along Lake Michigan and includes access to Ohio Street Beach, Oak Street Beach, and very close to North Avenue Beach.

If Navy Pier and/or beach time is a big part of your Chicago itinerary, I’d consider staying in Gold Coast to be within walking distance of both.

Side story: before I moved to the South Loop, I looked for an apartment in Gold Coast. The only apartment I could afford required my stove to be about 10 feet from my bed. Needless to say, I turned it down.

Kayaking at north avenue beach
Kayaking at North Avenue Beach

Lincoln Park

Lincoln Park seems to be a huge sought-after northern neighborhood to live in. I never saw the appeal (I prefered the more southern areas), but this is a mostly residential area. However, this is where you’ll go if you want to visit Lincoln Park Zoo.


Wrigleyville is technically within Lakeview, but it’s really the only part of Lakeview worth visiting (the rest is residential).

If you’re into lively nightlife and/or sports, PLEASE stay in this neighborhood! This is where the Cubs Stadium is located and when there are home games, the nearby bars and restaurants get wild! Heck, even when there isn’t a home game, it gets wild.

We used to come up here a lot in college and it never disappointed!


Another notable nightlife area. Boystown is very close to Wrigleyville and is home to LGBTQ-friendly bars and clubs. According to Wikipedia, Boystown is one of the largest LGBTQ+ communities in the nation!


While Bridgeport does have some great brunch spots, I only found that out because I lived near it the entire time I lived in Chicago. The reason you might find yourself in this area is if you plan to attend a White Sox game since this is where their Stadium is.


China Town is just North of Bridgeport and definitely has a different vibe than the rest of the neighborhoods on this list. As I’m sure you could guess, this is a primarily Chinese neighborhood and is the second-oldest Chinese settlement in the nation, behind California.

You’ll find GREAT food in this area and some interesting nightlife including karaoke.

Where to Stay in the City

I, unfortunately, don’t have any specific hotel recommendations in Chicago for this guide, but I can recommend neighborhoods based on what you’re coming to Chicago for in the first place.

If you’re coming for shopping, beaches, and fine dining, I’d stay in Gold Coast. Like I mentioned above, this area runs along lake Michigan, is home to luxury shops, and has several fancy and delicious restaurants.

If you’re visiting for nightlife or sports, I’d stay in Wrigleyville. This area is so fun at night – especially when the cubs are playing. You can go to the game and then walk across the street to a ton of bars with great atmosphere.

If you’re going to experience the different cultures of Chicago, I’d stay in the South Loop. You’re close enough to Bridgeport and Chinatown that you can experience these neighborhoods and understand just how much they differ from the rest of the city. You’re also very close to a few major attractions: Shedd Aquarium and Adler Planetarium as well as a short drive from the other major parts of the city like Navy Pier, North Avenue Beach, and more.

Biggest Tourist Attractions in Chicago

As I’ve been typing out this Chicago guide so far, I’ve mentioned a lot of areas good for eating and nightlife, but there is so much more to do in the city! Here are some of the highlights:

Architecture Boat Tour

If you haven’t heard of this tour before, you might roll your eyes like I did when my mom first suggested it! BUT there is a reason why so many people suggest it. It’s awesome! You ride on the Chicago River and the tour guide gives you some really interesting facts about the different buildings along the river.

If you’re not sold already, there’s a bar onboard.

Learn more about it here!

Willis Tower Skydeck

Willis Tower (or “Sears Tower” as it will always be known as) is the tallest building in Chicago. The Skydeck gives you a chance to see nearly all of Chicago from above. The glass floors in this area let you feel like you’re floating above the entire city.

Learn more about it here!

360 Chicago’s TILT!

Chicago 360 is located right on Michigan Avenue and this ride physically tilts you over the edge of the building so you can see straight down. Don’t worry, it’s completely enclosed and 100% safe.

There is even a bar called Bar 94 with 360 degree views of the city to stop in after you tilt!

Learn more about it here!

Navy Pier

If you’ve seen the iconic Chicago Skyline with the ferris wheel in it, that’s at Navy Pier. The current Ferris Wheel is actually the 3rd one that Navy Pier has seen – the first one being built all way back in the 1800s.

Aside from the Ferris Wheel ride, there are a bunch of vendors to walk around and see on the pier. There are also fireworks every Saturday in the summer to sit and watch.

You’ll also see Chicago Children’s Museum and Crystal Gardens in the building at the very beginning of Navy Pier. The Children’s Museum is obviously a great choice if you have kids with you. The Crystal Gardens is an indoor garden that’s nice to walk around and get away from the bustle of the city.

Learn more about it here!

Crystal Gardens at Navy Pier
Crystal Gardens at Navy Pier

Adler Planetarium

The Adler Planetarium is a must-visit in my book. It’s further south than most other activities – close to the South Loop and the Chicago Bears’ Stadium. This museum is fun for both kids and adults and you’ll leave with some new knowledge about planets, astronomy, and space in general.

They even do an event once a month called Adler After Dark for adults only. These are usually themed events and let you take in the exhibits with a drink in hand!

You’ll also find some of the best skyline views from the Planetarium.

Learn more about it here!

Art Institute of Chicago

The Art Institute of Chicago is an amazing art museum right in the heart of Chicago. They have pieces from all over the world and from all different time periods.

The Art Institute is also very close to Buckingham Fountain in Grant Park, so I’d recommend walking to the fountain from the museum in one afternoon.

Learn more about it here!

Millenium Park

If you’ve ever heard of “The Bean,” (actually called Cloud Gate) this is where it’s located. Cloud Gate is a humongous bean-shaped metal structure. Crowds of tourist flock here to take their photo in its reflection.

Millenium park also has gardens and other rotating art structures. They even host special events and concerts in the amphitheater space. It’s also a great place for ice skating in the winter.

Learn more about it here!

Shedd Aquarium

The Shedd is very close to Adler Planetarium in Museum Campus right on Lake Michigan.

This Aquarium is pretty impressive with a vast selection of fresh water and salt water marine life.

Learn more about it here!

There are a ton of other popular tourist attractions in the city including the Field Museum, Museum of Science and Industry, Lincoln Park Zoo, and more. However, if you only have a short time in the city, the above attractions are what I would focus on seeing.

Where to Eat and Drink in Chicago

Now, this is where things get a little tough. As you can probably imagine, there are SO MANY restaurants and bars in the city that it’s impossible to see them all. Pretty much anywhere you eat downtown is going to be good, so these are the places that really stuck out to me and I recommend to anyone visiting the city.

For Breakfast/Brunch

If you’re into a club-vibe early in the day, there’s no better place to plan brunch than Fremont. It’s buffet style with great food and when you’re done, head upstairs to continue your bottomless mimosas and dance the…morning…away!

If you’re looking for a more low-key option with great food, Nana is amazing. It’s in Bridgeport (so, way South of Fremont) and their menu is Latin-inspired brunch. This was a staple of mine when I lived in the South Loop.

If you’re looking to splurge, I’m actually confident in saying Shaw’s Crab House has the BEST brunch buffet in the city. Austin’s old boss turned us on to this place for brunch (it’s typically a fancy dinner place) and we’ve recommended it so many times. They have different rooms featuring different types of food including American breakfast food, seafood, sushi, crab legs, lobster bisque, a dessert station, and so much more. It’s a bit pricey, but seriously worth it.

Last, but CERTAINLY not least: Maison Marcel. This French-themed breakfast/brunch cafe is our FAVORITE cafe in the entire city. It is very cute, they serve macaroons, and the brunch is incredible. Just go – you won’t regret it!

Nana cafe in Chicago
Nana cafe for brunch

For Dinner

Austin and I have tried our fair share of steakhouses in Chicago and our favorite by far is Chicago Chop House. It’s got a 1950’s feel and the food is simply amazing. There’s no other place like it in the city.

Russian Tea Time is another favorite of ours. You probably won’t find this place on any of the “Top Chicago Restaurants” lists, but it’s so dang good! Hearty Russian food is such a delight on a cold winter day. They also do full tea service which is so cute and delicious.

If you’re in the mood for Italian, head over to La Scarola. They have the most authentic, mouth-watering Italian food I’ve had in the city and their portion sizes are big enough to have leftovers. Just make sure to make a reservation because they fill up fast.

One more Italian place that I can’t not add to this list is Tuscany. This quaint little restaurant near my old university is perfect for any occasion and the food and service are unmatched.

If you’re a sushi lover, I highly suggest you try Tanoshii. It’s in the West Loop and it’s THE best sushi I’ve ever had. I recommend opting for their Omakase which is where you tell the waiter your taste preferences and the chef makes you what he knows you’ll like. Everything we had was incredible.

And just because a Chicago guide wouldn’t be complete without it: DEEP DISH PIZZA. Listen, everyone that lives in Chicago has a different opinion about deep dish pizza. My favorite happens to be Lou Malnati’s, but you’ll find that half the people you talk to say Giordano’s is the best. Both are very good, so you won’t go wrong with either.

Like I mentioned above, you’ll find good food anywhere you go in the city – especially downtown. These places just happen to give me an experience above and beyond and that’s why they remain my favorite restaurants in the city.

For Drinks

We can’t forget drinks in a city that does nightlife so well! Before I start this section, I want to add that if you’re out drinking late, PLEASE splurge for an Uber ride home. You can take public transportation and it will probably be safe, but the Uber is likely about $5 more. Just be smart about it.

If you’re looking for a rooftop (which you should be if it’s warm), I’d try London House or Cindy’s. London House will give you incredible views of the city and Cindy’s shows off Lake Michigan.

Three Dots and a Dash is a fan favorite. It’s an underground tiki bar with tropical drinks to match. There are also a ton of other bars in the area like Howl at the Moon, Boss Bar, and more if you want to bar hop.

If you’re looking to really let loose and dance, Nacional 27 was always our go-to for Latin music.

I also mentioned that Wrigleyville is really good for nightlife. The place I recommend starting at is Sluggers. It’s a sports bar and even has batting cages for you to try (which is why I recommend STARTING here!). When you’re done there, just make your way down Clark St. – there are plenty of bars to choose from.

Three Dots and a Dash
Drinks at Three Dots and a Dash

You’re gunna love this city

What’s that saying – you don’t know what you have until you’ve lost it? That’s exactly how I feel about Chicago. I lived there for eight years and I don’t feel like I even put a DENT in seeing the whole city. So, don’t feel bad if you don’t see it all either. That’s just an excuse to keep coming back!

I hope you enjoyed this Chicago guide! Let me know what you plan to do on your next trip to Chicago in the comments below!

Love this Post? Pin it!

Leave a Comment

The Comments

  • Krista
    September 16, 2020

    I still need to visit Chicago and love hearing ideas from a local’s perspective! Thanks for the great tips.

  • Shay
    September 16, 2020

    This definitely has me missing Chicago big time! That photo kayaking on the water is stunning. I would love to do that!

    • saraharnstein
      > Shay
      September 16, 2020

      Ahh yes! The kayaking was so fun! I was missing Chicago as I wrote it, too

  • Laurel
    September 16, 2020

    Girl, this post is SO GOOD! SO in-depth! I have always wanted to visit Chicago and now I will know all the best spots to visit when I’m able. :))))

    • saraharnstein
      > Laurel
      September 16, 2020

      THANK YOU! And yesss you still need to go!

  • Olivia
    September 17, 2020

    LOVE this post! I’ve been to Chicago many times but haven’t even done half the things in this guide. Also, I’ve been dying to go on the architecture boat tour – hoping to do that soon!

    • saraharnstein
      > Olivia
      September 17, 2020

      Yess! The Architecture tour is so good!!

  • Jocelyn
    September 17, 2020

    This post is SO good!! I loved the history lesson!! Hope I get to visit soon 🙂

    • saraharnstein
      > Jocelyn
      September 17, 2020

      Thank you so much! I hope you can visit soon, too!

  • Josy A
    September 17, 2020

    Wowza! What a post!

    It is always nice to hear about a city from someone who has lived there for a while, but i just learned loads from this! I didn’t even know that you have “loops” for neighborhoods. Now i am always going to think of Chicago as a little loopy. 😉

    I love the look of the architecture and oooh your foodie suggestions sound fab!

    • saraharnstein
      > Josy A
      September 17, 2020

      Thank you so much for reading! Chicago is a little loopy, but that’s why we love it 🍷

  • Jenni / Out in the Nature
    September 28, 2020

    Chicago is most likely the next destination in the US that I will visit. I will visit a friend in that area and definitely spend few days exploring the city. So thank you for the tips, I will pin this for later!

    • saraharnstein
      > Jenni / Out in the Nature
      September 28, 2020

      Have so much fun! I definitely miss living in the city. You will love it!

  • Sophie
    October 15, 2020

    I actually had no idea that it had been burned down – that’s interesting that the rumour is that it was a cow! I’d love to visit Chicago – I definitely need to try the pizza and the Crystal Gardens look beautiful. I’ve also seen lots of photos of the skydeck which looks really cool! Thanks for providing so many other great ideas too 🙂

  • Megan
    October 31, 2020

    Chicago is SUCH a fun city! I’ve been to many of these awesome places, and it seems I’ve missed a few as well! I love it at Christmas time as well, despite freezing!