For those that know nothing about Chicago.

Anybody who’s lived in Chicago for more than a couple years could probably tell you everything below. But they probably won’t. Also, you’re an adult and have access to Google. But if you know nothing about Chicago and want a lot of information in one place, here it is…

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Intro to Chicago

In short, it’s so easy to have a good time in Chicago, but if you don’t know what your getting yourself into, you may not have a  great time. If you want to have a great time in Chicago, STAY IN THE CITY, BE PREPARED TO WALK A LOT, EAT GOOD FOOD, DRINK GOOD DRINKS, WALK AROUND NEIGHBORHOODS AND CHECK OUT SOME SIGHTS. The summers are amazing, and yes winter time will be cold so bring a good coat and hat.

Generally, Chicago is broken up into neighborhoods, each with a very distinct feel and pretty rigidly defined. You have to check out at least a couple different ones. Everything runs on a street grid system so basically you know where a place is by the street number (I.e. the higher the number, the farther away from downtown so 95th Street is far but 150th is farther). Chicago is also, basically, broken up into two cities, the North Side and the South Side (there is also the West Side, which blends into both).

Public transportation via the Elevated Trains (the “L”) and bus is pretty dang good – Google maps will tell you exactly which one to take. You shouldn’t rent a car. Lake Michigan is to the east and there is the Chicago River that basically outlines The Loop (Downtown Chicago) that runs from the top of the center of the city, north and south.

There are a few must-see landmarks, lots of places you should eat and drink, shows and entertainment, and a whole lot of places to walk around. I’ll give you the must-see’s further below. 

Where to Stay

Preferably you’ll STAY IN “THE CITY” somewhere – a safe bet is in Lakeview, Lincoln Park or just close to The Loop. It’s actually a pretty small area to stay in (relative to cities like Dallas and Los Angeles) but AirBnb is the best way to go. Stay on the North Side, don’t mess with anything lower than the Loop (downtown area). Staying by or at the airports is okay, but you’ll be far from the action. As I said before, don’t rent a car. You don’t want to deal with parking and traffic headaches when the CTA is so good and Ubers/Lyft pretty cheap.

Getting Around Chicago

The L

The L (short for “Elevated Lines”) a.k.a. the CTA, is the easiest way to get around Chicago. Our recommendation is to buy a Ventra card at the CTA vending machine at the station. These cost $5 but you can get this back in credit if you download the Ventra app and register the card (it’s super easy). Fares are $2.50 or 25c for transfers within 2 hours. You can top up at the station or via the app.


There are loads of bus routes nearby and you can use your Ventra card to pay $2.25 or 25c for transfers within 2 hours.

Uber and Lyft

Generally pretty cheap, especially if you choose the “Pool” or “Line” option (carpooling). Be aware that sometimes the GPS can be a little inaccurate if you’re ordering a ride from the Loop (due to the tall buildings and “lower” streets).

Divvy Bikes

You can get a full day’s worth for around $15.00 and Chicago is a very bikeable city (flat, with lots of bike lanes). While you may not be biking back to your hotel, biking to the beach and around downtown is a great time.

What You Should Do While Here

What you want to do generally is EAT GOOD FOOD, DRINK GOOD DRINKS, WALK AROUND NEIGHBORHOODS AND CHECK OUT SOME SIGHTS preferably while eating and drinking. But if you want to be able to tell people you saw and did the “big things” in Chicago, you need to:

  1. See “The Bean” at Millennium Park
    1. Start by heading to the Bean and then see a bit of Millennium Park and the surrounding area. There is actually not much more to see at the Park and nearby Grant Park, but it’s cool nonetheless. Plus you’ll be in the Loop with all the big buildings.
  2. Get deep dish and a Chicago hot dog
    1. Lou Malnati’s and Weiner Circle. Don’t mess around until you’ve established those baselines. Two slices or two dogs will almost always be enough. Do not mess around with appetizers. Don’t ask for ketchup – you don’t need it anyway.
  3. Check out Magnificent Mile and the John Hancock Tower
    1. Start by heading to and go up the John Hancock Tower to the Signature Lounge and get a drink. It’s way better than the Willis (Sears) Tower. There is no “admission” to the Signature Lounge, and you just have to act like you’re getting a drink or actually sit down for a drink.
    2. Mag Mile is a stretch of Michigan Avenue and made up of a bunch of cool shops that is good to walk. Walk South from the Hancock tower towards downtown. Also, unless you’re loaded, you’ll find better shopping on State Street in the Loop.
    3. Check out the Water Tower, which is just a cool looking building.  
  4. Check out a rooftop bar
    1. Cindy’s Rooftop bar is right by Millennium Park and has a great view of the bean. It gets absolutely packed after work but if you going during nonpeak hours, you’ll be okay. If not, try the J Parker, more below. Find others through Google.
  5. Check out Lincoln Park, Lincoln Park Zoo, and Lincoln Park Conservatory
    1. The J Parker is right by the main entrance to Lincoln Park Zoo. It gives an amazing view of Lincoln Park.
    2. You can also try to get Chicago Pizza and Oven Grinder around this time.
      1. Home of the Pizza Pot Pie.  Cash only and usually a crazy long wait, but put your name down and head to the J Parker to wait.
  6. Check out the Lakefront
    1. Feels like a beach on the ocean. Probably the most underrated asset of Chicago. Can do right before Lincoln Park Zoo. Goes without saying, during the winter expect only visuals.
    2. On that note, if it’s summer, then you absolutely get in some beach time. My suggestion is North Avenue Beach if you want the most popular one or Hollywood Beach if you want what I consider the nicest one.
  7. Check out a Brewery
    1. There are so many really neat places. Metropolitan Brewery is stunning, but a little out of the way. Lagunitas is a fun trip in many ways. Forbideen Root is a great place to eat and drink. Off Color’s Mousetrap has amazing beer. Goose Island is a classic.
  8. Go to the Adler Planetarium for one of the best views of the skyline. Might as well check out the actual Planetarium while you’re at it.
  9. Check out different Chicago neighborhoods and take a walk. Each neighborhood provides such a different look at Chicago. To list three:
    1. Lakeview – Walk west to east on Belmont and north or south on Clark. East and west on Diversey street used to be my recommendation.
    2. Wicker Park – Walk north to south on Milwaukee.
    3. Logan Square – Walk north to south on Milwaukee, but further north.
  10. Check out the Cubs Stadium, Wrigleyfield and get a beer at a nearby bar.
    1. Ideally, you’d visit during July or August when there are games going on. You would also buy a cheap ticket and sit in the bleachers drinking good, but overpriced, beer.
  11. If you’re into sports, also check out the Bears stadium, Soldier Field. You can stop in by nearby museums as well.
  12. If the weather is decent, an early morning architecture boat tour is the best way to get a feeling of Chicago.
    1. You can also walk along the riverfront but many things will be closed if it’s winter and cold.
  13. It’s worth saying, if it’s summer you must hit up one of the many street festivals. There are too many to list here.
  14. Go to Navy Pier. It’s not the most adventurous thing you’ll ever do but, and I hate to say this, you have to knock it off the list.
  15. Don’t go up the Sears Tower. At least I don’t recommend it. It is out of the way and only worth seeing from outside. Inside is just alright to check out but you will get a better view of the city at the John Hancock Tower and it will be free and less crowded. This bears repeating.

What You Really Shouldn’t Do While Here

  1. DON’T GO TO A MUSEUM. Yes, even the art museum. There are far better things to do with your time and, sadly, far better museums out there. Avoid the lines, high prices, and check in somewhere else. If you have to (because you have kids or for some other reason), go to the Museum of Science and Industry and do not miss the U-Boat exhibit. 
  2. DON’T GO UP THE SEARS (WILLIS) TOWER. It seems cool, it actually is cool, but it’s really one of the few tourist traps in Chicago. It’s overpriced, really crowded, and you’ll wait forever to spend 25 mins up there. Go to the Signature Lounge at the John Hancock Tower instead.
  3. DON’T GO TO THE SOUTHSIDE. It’s sad to say, but Chicago is basically cut into two parts. The Southside and far Westside (Englewood and Garfield Park/Austin) are dealing with and account for the large majority of the serious crime in Chicago. There isn’t much to see there so you should stay clear, unless you know someone who lives there. This does not apply to Chinatown or Pilsen.

How to Choose a Bar

  1. If you want to be FANCY, impress your parents, or blow a lot of money at a club, check out the River North area. My suggestion for the former is Gilt bar or LondonHouse Rooftop and for the latter, TAO Chicago or Untitled.
  2. If you want to be MODERN POSH, hang out with young professionals dressed nicely while drinking an overpriced beer, check out Oldtown. My suggestion is The Vig or any bar nearby on Wells Street.
  3. If you want to be a BEER SNOB, and enjoy some of the finest breweries in the country, check out West Loop. Disclaimer: there are amazing places all over. My suggestion is Lagunitas or Mouse Trap, ironically, neither are in West Loop. 
  4. If you want to sip on FANCY COCKTAILS, and say things like amaretto and charcuterie, check out West Loop. If you can get a seat, try the Aviary, if you can’t, try Violet Hour.
  5. If you want to spend time around other DRUNKS, feel like a true Cubbie fan, and bar hop on the same stretch of street, go to Wrigleyville. My suggestion is Cubbie Bear or Sluggers, or any bar along Clark Street.
  6. If you want to see some HIPSTER DIVE bars with a diversity of vibes and drinks, check out Wicker Park. My suggestion is Phyllis’ Musical Inn or any bar along Division Street.
  7. If you want CLASSIC AND COLLEGE BARS, dotted around a larger area that you’ll have to uber in-between, and intermixed with some of the best college bars, go to Lincoln Park. My suggestion is The Apartment or any bar nearby, or Gaslight bar & Grille.
  8. If you want some HIP AND UNIQUE bars go to Logan Square. Many can also be found in Wicker Park, and really throughout Chicago. My suggestion is The Whistler or The Owl.
  9. If you want your TRUE DIVE bars, complete with who appear to be “townies,” go to Bucktown. My suggestion is the Tap Room. Many can also be found throughout Chicago, namely, Old Town Ale House. 

If want a full day of activities, I can recommend the below. We call it the Walk (for a reason):

Start by having breakfast in Lakeview East, options are limitless, then,

  1. Walk east on Diversey Parkway from Clark Street and Broadway Avenue towards the lake.
    1. You should be using Google Maps to see exactly where you’re going.
  2. You’ll hit Lincoln Park and two awesome statues. Stop by the Elks Memorial Lodge (dome building with weird hours) at Diversey and Lakeview Avenue.
  3. Continue south into and through Lincoln park, towards the Fullerton Avenue. Once at Fullerton Avenue, go east towards the lake for an amazing view.
    1. Optional: Check out Lincoln Park pond, Lincoln Park Zoo and Conservatory beforehand and head east once at the south exit of Lincoln Park Zoo. Use Google maps.
  4. Once at the lake, walk south along the Lake Front Trail (towards the city).
  5. Head to the John Hancock Tower on Michigan Avenue. Again, use Google Maps. 
  6. Go up the John Hancock Tower and enjoy a drink at the Signature Lounge. Ask around if you need to.
  7. Walk south along Michigan Avenue to the Chicago River.
  8. Once at the river go down to the River Walk on the southside (closest to the city) of the River.
    1. Optional: Head east to Navy Pier.
  9. Go west on the River Walk.
  10. Come back up the stairs at LaSalle Street. One more time folks, Google maps. 
  11. Go south to the Cadillac Theater, see the sign, then go into the Thompson Center.
  12. Head down into the food court of the Thompson Center and head south into and through the Pedway underground.
  13. Walk through the pedway into City Hall and come up there. It’s okay to get a little lost. That’s Chicago, baby.
  14. Walk out of City Hall and head east towards the Daley Center Plaza. There will likely be something going on there.
  15. Go north to Randolph Street and head east on it.
  16. Stop at State Street and check out the Chicago Theater sign.
    1. Optional: Do some shopping on State Street to the south.
  17. Continue East on Randolph Street and head to the Chicago Cultural Center at Randolph and Michigan.
  18. Spend a decent amount of time exploring the Chicago Cultural Center and see the world’s largest Tiffany Glass Dome.
  19. Come out and head east to Michigan Avenue. Head a short block south on Michigan Avenue to Washington Street.
  20. Head east on Washington Street into Millenium Park.
  21. Go to the Bean. You can find it, I promise.
  22. Check out Millenium Park, walking south.
  23. Go to the Crown Fountain (Face Fountains) at Millenium Park. Stop for a bit.
  24. Double back a bit to Cindy’s Rooftop Bar overlooking Millennium Park. Do this only if it’s nonpeak hours.
    1. Optional: Head south to Buckingham Fountain.
  25. Once done, uber straight to the best restaurant you can find. Hopefully where you already have reservations using OpenTable.

Some General Short Tips to Remember

  1. Be prepared to walk. It’s a great walking city and you can get so much out of it.
  2. Chicago is pretty safe in the north neighborhoods, but it’s still a big city. That means always be on alert. Especially when on public transportation.
  3. The weather in the summer is usually great – maybe a little warm and humid on some days, but very nice nonetheless. Winter is very cold. Best time to be here is July, better in late-July.
  4. NEVER leave anything in the car, no matter in what neighborhood.
  5. One of the coolest views of the City is from where the Adler Planetarium is located.
  6. NEVER ask for ketchup on your hotdog.
  7. Deep Dish is great, but a lot of people think it’s overrated. Just making that clear. There is not “one” deep dish spot, but many that claim to be the best and or the original.
  8. Chicago does have beaches and quite a few of them. But occasionally they are shut down during the summer and closed after Labor Day.
  9. The Southside and Westside are actually dangerous.
  10. Chicago is broken up into neighborhoods and each one has a very unique atmosphere.
  11. People can be mean in Chicago, but generally it’s a very friendly city.
  12. There actually isn’t much on gangsters as far as Museums and Landmarks. I think Chicago has tried to get away from having that reputation.
  13. See if you can pick up on this, but there is a huge rivalry between Chicago and New York. Chicago has always tried to prove it’s just as good, if not better, than New York. And new Yorkers have always looked down on Chicago. In my humble opinion, I live here and not there for a reason.


Here are some Chicago geographic areas and terms that I seem to explain time and time again:

Lakeview Neighborhood

  • Northside Chicago by the lake but also goes west closer to the river. Nice nightlife, young and vibrant.
  • Home to Boystown, which is the gay district. A lot of fun.
  • Home to Wrigleyville and Wriglyfield, although Wrigleyville is generally considered a separate and different neighborhood.
  • Nice, mostly inexpensive local restaurants and very cheap bars.

Lincoln Park

  • Neighborhood, which I consider at least, to be the most residential.
  • Northside Chicago, very nice, slightly more expensive version of lakeview.
  • Lakeview and Lincoln park are right next to each other, separated by Diversey street. Runs along lake but also goes west closer to the river.
  • Home to Lincoln Park, Lincoln Park Zoo.
  • Has a great, but more expensive generally, bar and restaurant scene.
  • Really nice looking neighborhoods, that are cool to stroll through.

The Loop

  • What people refer to as The Loop means Downtown Chicago. It got its name from the loop of elevated trains that circle it.
  • Most people work here, but a lot of professionals also live here.
  • Is closed in by the Chicago River to the north and west, and Lake Michigan to the east. There is no “east Chicago,” that’s the lake.
  • Home to The Bean (Cloudgate), Willis (Sears) Tower, Trump Tower (technically in River North), and most of the tall buildings, Millenium Park, Grant Park, all the museums (e.g., Art Museum, Field Museum, Adler Planetarium, but not Museum of Science and Industry), Macy’s building. There is truly some great architecture and sights in the loop.
  • There is State street which provides great shopping, but the best shopping street is out of the Loop in River North Neighborhood on Michigan Avenue.
  • The really expensive restaurants are to the north as well, in River North Neighborhood, and to the west in West Loop (technically outside the loop).
  • To the south of the Loop is really where all the danger is. But also south of the loop are Chinatown and Pilsen neighborhoods.
  • A good amount to see.


  • Northside Chicago, nice bourgeoises neighborhood where rich older people live.
  • Has a really nice bar and restaurant scene, but not as pricey/”nice” as River North neighborhood.

Wicker Park

  • West of Lakeview. Just hard to get to from the Northeast side of town.
  • A very unique, up and coming neighborhood, with hipster and new age shops, restaurants and bars.
  • They have a lot of cool fairs, festivals and shops here.
  • Gentrified neighborhood, close to other up-and-coming gentrified neighborhoods such as Bucktown and Ukranian village.

River North

  • Neighborhood just north of the Loop and north of the Chicago River.
  • Probably the most expensive neighborhood. Has a reputation for being very posh and over the top.
  • Home to The Magnificent Mile on Michigan Ave., which is probably the highest end shopping district.
  • Some cool sights, but you don’t need to spend a long time here.

North Avenue Beach

  • Big beach next to Lincoln Park
  • Pretty nice, can get very crowded as its one of the top beaches.
  • Lots and lots of volleyball nets.
  • Kind of separated from everywhere else, so come prepared.
  • Home to Castaways and Shore Club. Great in the summer and I recommend checking out.

Hollywood Beach

  • Probably my favorite beach, and the most comparable to what other beaches are like in Florida.
  • Pretty big but about 15 minute drive north; north even of Wrigley.

Oak Street Beach

  • The party beach – small.

Navy Pier

  • Just north of the Loop, technically in a neighborhood called Streeterville next to River North.
  • Home to the Chicago Ferris wheel, a long mall with some alright stuff, lots of boats dock here, and there are some cool sights.

United Center

  • In the Near West Side neighborhood, west of the Loop.
  • Where the Bulls and Chicago Blawkhawks play. A cool venue but it is kind of far from most things. Is close to some bars and restaurants though.
  • Hosts concerts.

The Southside

  • Basically anything south of the Loop – but many Chicagoans would yell at me for defining it as such.
  • Generally the “dangerous” neighborhoods. Will also get yelled at for this.
  • There are many many neighborhoods with their own names in the Southside and also areas generally known as “Out South” and “Down South”

The Westside

  • Basically anything west of West Loop
  • Also the “dangerous” neighborhoods. I don’t think I will get yelled out for this.
  • Many neighborhoods with their own names.

Neighborhood and Street Festivals

  • Live music, food and drink vendors, sometimes people open up their backyards to visitors. Always check one out if you can.