Chicago
This obviously had to be my first blog post. I moved across the United States from Oklahoma to Chicago. I fell in love with this city fast. I used to think I would only be here a few years, but here I am 5 years later & I just signed another lease. Let the adventures continue!
There is truly nothing like Chicago. There is always something to do here.. it’s a foodies dream, festivals all summer, sports year round, great theater, comedy clubs, museums, amazing rooftops, beaches in the heart of the city, so many different neighborhoods, the list goes on & on.
First thing that comes to mind when visiting is of course all of the typical “touristy” things.
Cloud Gate AKA The Bean! The John Hancock building, Willis Tower, Museums, Millennium Park, Michigan Avenue “The Magnificent Mile”, the Riverwalk, Navy Pier, Wrigleyville, Lincoln Park Zoo. There is so much you can do & see for free including Lincoln Park Zoo!
The Bean
Chicago Theater & Macy’s on State Street
The Riverwalk
Navy Pier
The City Pass is a good way to see the city. It is around $100, but it is an all-in-one pass. You can choose options of what you want to see. When my boyfriend first visited me in Chicago we did the Shedd Aquarium, Skydeck, Field Museum & Adler Planetarium all in one day. So it was a busy day, but we got to see a lot in a short amount of time.
Shedd Aquarium
Skydeck
Field Museum
Adler Planetarium
It gives you the option to visit Art Institute instead of the Adler Planetarium, which is what I would recommend. Also included is the option to visit the Museum of Science & Industry or 360 Observation Deck.
Art Institute
Hidden Gem 💎 When we have visitors in Chicago we always take them to The Signature Room on the 97th floor at the John Hancock building to get drinks & the best views of Chicago. If you don’t get a City Pass & are debating between the John Hancock Tower & The Willis Tower.. go to the John Hancock Tower. You can go up to the Signature Room Lounge & purchase a drink (around $10 each minimum) & you get the views for free! Also, the women’s bathroom has some of the best views in the city ladies!!
Comedy shows come to mind to a lot of people when you mention Chicago, specifically at The Second City. Some of the greats have came out of The Second City including Chris Farley, Mike Myers, Bill Murray, John Belushi, Dan Aykroyd, Steve Carrell, Joan Rivers, Tina Fey, Amy Poeler to name a few!! They have different shows you can see multiple nights a week!
Laugh Factory is another comedy club that I really liked. They frequently have celebrity guests & they have “The Nasty Show” for the late night show, which I have seen a few times & it’s hilarious.
SUMMER TIME CHI
The best time of year to go is in the summer time of course! Since the nice weather only lasts about 3 months you have to make the most of it. There are food & music festivals every weekend including Lollapalooza, Jazz, Taste of Greektown & Taste of Chicago to name a few. Choose Chicago is a great reference for this.
Country LakeShake is in June for my fellow country music fans! We went this last year & had so much fun. It’s a 3 day festival of country music right in the heart of the city. Prepare to get your boots dirty! Rain or shine.
Beautiful weather means hanging out on the beaches, patios & rooftops. The Lakefront trail is a great place to go for a walk or bike ride & see some amazing views of the city (there are Divvy bikes all throughout the city you can rent for up to 24 hours)!
St. Patrick’s Day in Chicago is where it’s at. They dye the Chicago River green every year & there are so many good Irish Pubs to go to!
If you feel like hitting some golf balls there is a TopGolf located in Wood Dale.. take train to Rosemont Blue Line station & then Uber/Lyft from there. This is to help save money instead of getting a ride all the way from downtown Chicago.
Catching a Chicago Cubs or Chicago White Sox baseball game is also an option!
My favorite beaches are North Avenue & Oak Street Beach.
North Avenue always has a lot going on & it is good for watching the Chicago Air & Water Show in August. It is one of my favorite weekends of the year!
Oak Street Beach is my personal favorite & is in the heart of the city.
Architecture river, sunset & booze cruises are such a fun way to see Chicago when its nice weather. Depending on what you are into, they are all good!
Memorial Day Booze Cruise on the Mystic Blue
LondonHouse - Rooftop overlooking downtown & the river. Year round.
IO Godfrey Rooftop Lounge - Year round, weather permitting.
Rockbottom Brewery - Summer time. In the heart of downtown.
The Robey - In the heart of Wicker Park & has a pool that overlooks the Chicago Skyline.
PIZZA 🍕
Deep dish
Giordano’s - My personal favorite & go-to everytime someone comes to visit. Recommend the Meat & More Meat with Sangria🍹
Lou Malnati’s - Famous Sausage pizza. Great patio in Gold Coast!
Pequod’s - I’ve never tried it, but i’ve heard its really good.
Not deep dish, but if your looking for a fun atmosphere & good pizza.
Happy Camper or Homeslice (same menus, different names)
Recommend the “Dime Piece / Smoke Show” - Blackened chicken, cream cheese & jalapeño pizza.
SPEAKEASIES
There’s so many I still have yet to go to, but here’s a few of my favorites so far.
The Drifter - Underground bar with limited seating. Different themes for shows nightly. Great cocktail menu.
Three Dots & a Dash - Underground tiki style bar.
Violet Hour - Modern speakeasy in Wicker Park.
On the list
The Green Mill - Famous speakeasy where Al Capone used to frequent. Jazz & cocktail lounge.
The Aviary - The Office
BRUNCH 🍾
Duffy’s - I have to give a shoutout since we lived right by Duffy’s for 2 years. Great bar for game days, happy hour & brunch specials. Around $30 ALL-YOU-CAN-EAT brunch buffet with beer, mimosas, bloody mary’s included. 10-3 Saturdays & Sundays. You can’t go wrong.
Lokal in Wicker park - Bottomless mimosas & rap music. Enough said.
Bongo Room - Pancakes & bloody mary’s are on point.
The Hampton Social - Perfect for brunch with the girls!
25 Degrees - $11 Champagne bottles from 10-3 Saturdays & Sundays. They have a garage that opens up when it’s nice outside. Recommend the Pork Eggs Benedict & Breakfast Quesadilla. They also have amazing burgers!
DATE NIGHT DINING
Shaw’s Crab House - Surf & Turf. Seriously heavenly.
Joe’s Stone Crab - Stone Crab in Chicago.. What more could you ask for?
RPM Italian - Guiliana & Bill Rancic’s Italian Restaurant.. One word, Carbonara.
Topo Gigio - Fine Italian Dining in Old Town! Soo good.
Roka Akor - Sushi. Scallops... They melt in your mouth!
CHICAGO EATS
Big Star in Wicker Park - Best margarita pitchers in Chicago & street tacos.
Santorini in Greektown - Best octopus we have ever tried. But really anywhere in Greektown I would recommend if you like Greek food!!
Cafe Ba-ba-Reeba - Tapas, small plates, Sangria.
Grand Lux Cafe - Great lunch or dinner spot. Santa Barbara chicken sandwich, steak caesar salad & pasta carbonara are all good choices. Ask for a table in the circular room past the bar overlooking Michigan Avenue!
Chicago is also known for their Italian Beef & Hot Dogs
Al’s Beef - Italian Beef. Get it dipped!
Portillo’s - Hot Dogs & Chocolate Cake Shakes
There are still so many places I have wanted to try in Chicago that I have heard about. Here’s a few of the top choices I would recommend.
WINTER TIME CHI
Chicago winters can be brutal, but I guess I have somewhat gotten used to them. Actually, I just hibernate in my apartment or fly somewhere warm, haha. I love Christmas time in Chicago though. It is still possible to visit in the winter & have a good time. The Christmas lights on the streets downtown are so pretty with the snow falling. It’s dreamy.
The Chriskindlmarket is amazing! We go for the German food & Gluhwein every year… You get to keep the mug with purchase!! They have so many amazing gifts for Christmas & ornaments that are awesome!
Zoo Lights & ice skating in the parks are also fun options. There are two different places downtown to ice skate including in front of Cloud Gate at the McCormick Tribune Plaza & Ice Rink & at Maggie Daley Park Skating Ribbon.
A fun bar to visit during Christmas time is Butch McGuires!
There is also a pop up bar, Frosty’s Christmas Bar which I plan on going to this year. Christmas-themed drinks, colorful lights & DJ music.
Catch a Chicago Bulls game!
Or Da Bears at Soldier Field!
A Blackhawk’s game is another option! I have still yet to go to one, but I have heard they are really fun.
Don’t let the cold weather scare you away, however I would suggest late November or December if you are coming in the winter!
WHERE TO STAY
Last but not least are some recommendations on where to stay. As I said before Chicago has a lot of neighborhoods that I didn’t know about until I moved here. Of course first thing that comes to mind is to stay downtown which is convenient, but it can be pricey.
I have stayed at the Sheraton downtown & it was a good hotel / decent price. We had a view looking over the lake & Navy Pier. It is right off the Riverwalk downtown, so it is a great location.
A few other neighborhoods to consider are:
Rosemont- By the airport & use Blue Line train to get downtown. Cheapest route.
Logan Square / Wicker Park - If you are considering Airbnb these are both great locations with shopping, restaurants, bars & close to Blue Line train as well.
Lakeview / Lincoln Park - If you are wanting to stay by the lake, Lincoln Park Zoo or close to Wrigley Field. Very easy to get downtown by Uber or multiple train/ bus routes.
I hope you guys enjoyed my very first blog post!
Life is short, book the flight.
xoxo, Tarah
