Chicago Travel Guide.

What To Do In Chicago Travel Guide

Chicago.  Just typing that word makes my heart flutter!

After my first visit in college (in the winter, no less!) I fell in love with that city and now, after taking the train into the city each week for work last year and spending many weekends exploring with Matt, I love it even more.  It’s truly such a gorgeous, fun, lively place that is fun all throughout the year and exudes a unique “feel” with each passing season.  If you haven’t visited yet, I can’t recommend it enough, though for your first time I would recommend the Summer or Fall months.  While totally do-able, the Winter isn’t for the faint of heart 😉

If you have a trip coming up or are just curious, below I’m sharing my guide to all things Chicago: what to see/do/eat/drink, where to stay, and what to skip.  Pin these photos for reference later and let me know if you’ve done any of these or take me up on any suggestions!

Taxis on Wacker Chicago



The Bean –  A completely free attraction located in Millenium Park just steps off of Lakeshore Drive, I will admit it is a total tourist move but I don’t even care – I am freaking obsessed with The Bean!  You’ve likely seen pictures of this unique oversized piece of art and it is even more entertaining in person.  It gets pretty crowded so if possible, the best times to go are early in the morning or on weekdays while people are at work.

The Bean Chicago Sunrise No Tourists

Chicago Athletic Association – If there is only one thing you do, you MUST go here!  Back in it’s prime this was a popular men’s club that has now been refurbished and is free and open to the public.  Located on Michigan Avenue just south of the river and directly across the street from The Bean, on the second floor of an unassuming building, it truly feels like a hidden gem.  Walking in feels like entering a Hogwarts library, filled with tables, leather couches, wool chairs, the works.  There is also a coffee shop open at select hours and in the back you’ll find a bar and game room complete with bocce ball, fooz ball, shuffle board, chess and more.  I highly recommend the frozen gin drink in the game room and the creme brulee in the main library room – it’s unbelievably delicious!

You won’t find signs for this secret spot so to get there, simply enter on the ground floor at Shake Shack, and go up the flight of stairs to the right.  You’ll find the club on the second floor.  The club also functions as a boutique hotel if you’re looking for a one-of-a-kind place to stay.  Basically this place does a little bit of everything!

Rent Divvy Bikes – For a small fee, you can rent a bike for the day.  The only catch is that you must return your bike and check out a different one every 30 minutes or you get charged (amount depends on how late past the 30 minutes).  But fear not!  There are bike stations all over the city making it extremely easy to check in and out.  For the cost it is well worth it.

I recommend biking along Lakeshore Trail which is a paved bike path that runs parallel to Lakeshore Drive and Lake Michigan.  It is a stunning ride with the water on one side and the city on the other.  We do this almost every time we go!

Rent Divvy Bikes Lakeshore Trail Chicago

Architecture boat tour – We still haven’t done this one but it is high on our list because everyone who has done it always raves about it!  Do yourself and favor and plan this for your next trip.

Restoration Hardware – Located in the Gold Coast, this is the only RH of it’s kind, complete with a restaurant, wine bar, rooftop, coffee shop, and of course a fully functioning store set up showroom-style.  The architecture of the building is absolutely incredible and every single space is just amazing.  Initially my husband was confused why I wanted to go here so badly but now we make a point to visit every time we are in the city.  If you eat there, I’ve heard the hamburger and the chocolate chip cookie are excellent.

Restoration Hardware Chicago 3 Arts Club

Head to the beach – During the Summer, you’ll find most Chicago residents hanging at one of its many beaches.  Since they know true Winter, when the sun is out and shining, you’ll find them savoring it!  Hang out, play some beach volleyball or hit up the beach club if you’re feeling adventurous (you’ll know it when you see it – or more accurately hear it, the music is always blasting!).  You can plop yourself anywhere along the shoreline, but we typically ended up at Oak Street Beach or North Avenue Beach.

One other option would be to rent a sail boat and head out on the lake.  We have never done this but it’s on my list because the view of the skyline from the water is truly breathtaking.

Riverwalk – The riverwalk is a paved walkway that runs along the south side of the river from Lakeshore Drive all the way to Franklin Street.  Since it is a pedestrian-only path you don’t have to worry about cars whizzing by on Wacker and you can enjoy a ton of amazing viewpoints (great for pictures 😉 )

Chicago Riverwalk Sunrise

Walk around DePaul’s campus – It may be just us, but we love visiting the college campuses in any place we visit.  DePaul’s campus is special because it is located right within the city and the Catholic Church on campus is absolutely beautiful.  If you have time it is just two blocks north of Armitage in Lincoln Park.

Cub’s game / Wrigleyville – If you plan your visit during baseball season, I highly recommend buying tickets to a Cub’s game.  I’ll let you in on a secret: the absolute best seats in the house are actually not in the stadium, they are the “bleachers” across the street (see photo below)!  Wrigley Field is located smack dab in the middle of an urban neighborhood and many of the surrounding townhouses have sold their roofs to companies who have installed stadium-style bleachers, many complete with concessions stands.  It’s such a unique experience and the view is actually really great.  We did it right before we moved away and it was one of my favorite Chicago memories!

If tickets are too pricey or it is too much of a time-commitment (why are baseball games so long?) I would recommend at least walking around Wrigleyville.  Feel free to hop from bar to bar or grab a bite to eat, though keep in mind the service may be a little slow because every place will be packed full of fans watching the game.  Chicago is such a sports city and they take so much pride in their teams!

Sunset from the Bleacher Seats at Wrigley Field



Breakfast / Brunch

Glazed and Infused – A donut shop with a few locations sprinkled throughout the city but we always visit the one on Armitage in Lincoln Park.  Their maple bar with bacon on top is my all-time favorite donut!

Stan’s Donuts – Again a few locations but we’ve only been to the one in Streeterville.  Stan’s is pricier than most donut shops but they have a ton of inventive flavors you won’t find elsewhere – I love the pistachio old fashioned!  Added bonus: the interior is Instagram heaven – can you say #ihavethisthingwithfloors?

Pistachio Donut Stan's Donuts Chicago

Beatrix – Located in River North, Beatrix has a really great brunch.  I suggest making a reservation because this place always gets packed – but that’s how you know it’s good!

 The Little Goat – Located in the West Loop, The Little Goat is the sister restaurant to the acclaimed Girl and the Goat located just across the street.  The Little Goat serves breakfast all day and has a more casual feel and more reasonable pricepoint than Girl and the Goat.  (If you are looking for a nice dinner though I do recommend GATG because I’ve only heard great things and have always wanted to go.  Just be sure to make reservations!  We tried to go once but waited until the day before to call and the only option was 10 PM!)

West Loop Chicago Street Style

– Coffee – If you’re looking for a cute cafe with a great cup of coffee, I recommend checking out this post from my friend Laura who lives in the city sharing her top 10 favorite places in the city.


Lunch / Dinner

Butcher and the Burger – Located in Lincoln Park, this is a build your own burger spot and the meat and everything is exceptional! The place is owned by a little old man who chatted our ears off the day we visited, he was adorable!  Large burgers for a very decent price.

Nando’s Peri Peri – Specializing in Portuguese flame-grilled chicken, Nando’s is great if you are on a carb-free diet and/or on a budget because your meal will be under $10 and while they do have a few other items on the menu, they pretty much just do their famous chicken.  This spot seats like a restaurant (with amazing decor to boot!) but you order at a counter and your food is brought to your table.  I recommend the 1/4 chicken, medium hot and if you order the fries be sure to get the Perinaise dipping sauce!

You’ll find two locations: one in the loop downtown and one in the West Loop (not to be confused with one another 😉 )

Nando's Peri Peri Chicago

City Winery – Located in the West Loop, they have a really cute patio that is open weather-permitting.  I’ve only been here for an event so I didn’t get the full restaurant or wine tasting experience, but the food was wonderful and the ambiance was amazing.

Green Street Smoked Meats – Still on our list to try, every person we ask who lives in the city always recommends this BBQ joint in the West Loop.

Avanti Caffe – If you find yourself in the loop downtown and are craving some quick Italian food, this authentic deli will do the trick!  There are a few tables inside but most people order to-go.  If you’re wondering what to order, get the meatballs!  I used to get them once a week when I worked down here.

Overcast Morning in The Loop Chicago

Lyfe Kitchen – With a few locations throughout the city, every time we passed one we used to make jokes because I can’t take the spelling seriously, but after trying it I am a fan!  Delicious food for a reasonable price.  I recommend the “unfried” chicken with brussels sprouts – if you are not starving, it is easily enough for two meals and priced at just around $12.  This is another spot that seats like a restaurant but you order at a counter.

Deep dish – Deep dish is an acquired taste, people either love it or hate it.  Personally I am in the latter camp but every once in a while you have to order it since it’s Chicago’s specialty. The two best places in my opinion are Lou Malnati’s and Pequod’s.  Keep in mind that deep dish takes about 45 minutes from the time you put in your order.  If you see a line outside, don’t be scared because oftentimes, they’ll take your order while you’re in line so they can get your pie in the oven and you don’t have to wait that additional 45 minutes once you’re seated.



Cindy’s – Best view of any rooftop bar in the city!  This is at the top floor of the Chicago Athletic Club (mentioned above) but you’ll have to take a separate elevator to get up to it.  Just go to the ground floor and ask someone.  I don’t know why they make it confusing but they do!  The food here is family style and honestly I think overpriced, but the drinks are standard price for the city ($10-15) and they have an incredible bar.  I haven’t actually drank here because we came here at like 10 am one time and another time with Matt’s parents but everything sounded SO good and the inside of the restaurant has the cutest ambiance and they have a big balcony with an incredible view (see below) and a fire pit.

Cindy's Rooftop View Chicago

Bar Siena – Located in the West Loop, they have a great Moscow Mule and I’ve heard the food is fantastic too.  This place is really cute inside, it is two stories and they have a tree that goes up the middle of the floor straight through to the second floor that is all lit up with string lights.

The Signature Lounge –  Located on the 96th floor of the Hancock Building on Michigan Avenue, this spot is one-of-a-kind.  To be honest the drinks aren’t anything special and are on the pricier side (around $15-20 a cocktail) but you are paying for the view.  The space features floor to ceiling windows and is located just a few blocks from the lakefront, so you have views over the lake and the entire city.  It is truly breathtaking.  We went at night and the view of all the city lights was incredible, but I think sunset would be even better!
Just so you are not shocked, you have to get in a line on the ground floor and take an elevator up to the 96th (the restaurant is located on the 95th).  However, the line moves fairly quickly so don’t be deterred.
Signature Lounge Hancock Building Chicago



Cone – An adorable ice cream shop in the West Loop, they have tons of fun flavors like Guinness and honey lavender (I believe flavors rotate throughout the year). Their most famous flavor is the bright blue one called “Cookie Monster” – it is delicious!

Cone Chicago Cookie Monster

Honestly not sure how I don’t have more “sweets” recommendations.  Need to work on that 😉



 Airbnb – If you’re looking for an authentic experience and want to feel like you “live” in Chicago during your visit, I recommend Airbnb.  We have tried a few different Airbnbs in the city and had mixed experiences so my recommendations are to pick what neighborhood you want to be in and make sure it is close to public transportation (unless you plan to Uber everywhere).  In our experience it was worth it to pay a little more for a neighborhood we really liked and that was close to the L because in the end we spent less getting around and were close to restaurants and bars we wanted to visit.  Hands-down our favorite neighborhood is Lincoln Park – think brownstones, cute boutiques, and restaurants and bars galore – so much charm!  Not far from either the lake or Wrigleyville, LP is well-located if you plan to do a lot of walking or just a quick Uber from most other places.

As for a specific Airbnb, I recommend this one.  Located on Armitage Street (the main drag in LP), directly above a shop, this place was our favorite and really put us right in the thick of it.  It is directly next door to the L station (so it was a little loud at night but we got used to it really fast and slept like babies) so it was insanely cheap and convenient to get all over the city and so convenient.

Areas I would recommend staying in would be Lincoln Park (mentioned above and where all the young people live), Streeterville which is close to Michigan Avenue and Wacker (Michigan Avenue itself is really touristy, but this would put you close to the water and in between downtown and LP), or Lakeview (neighborhood right next to LP, this is right on the water).

Christmas Decorations Lincoln Park Chicago

Hotel Lincoln – Located at the edge of Old Town/Lincoln Park, this funky boutique hotel is a great choice if you’re looking for a space with a unique flair.  The walls are covered in local and vintage artwork and the rooms feature Jonathan Adler bath products.  The rooftop bar has a great view over the zoo and the lake and they also have bikes on hand for guests to use.

Hotel Lincoln Chicago

The Freehand – If you’re looking for an inexpensive place to stay I can’t recommend The Freehand enough.  It is a hostel that features both shared rooms and private rooms (shared rooms are obviously cheaper) and everything about the place is fantastic.  From the decor to the staff to the value, this place can’t be beat.  The lobby and main commune area seriously looks like something out of an Anthropologie catalog!  They also have a restaurant and bar called The Broken Shaker which is supposed to be really great as well as a coffee shop called Cafe Integral.

When I had to travel into the city every Monday and stay just for the night this is where I stayed.  It is centrally located within the city and a bed in a 4-person all girl room only put me back about $20 a night.



Michigan Avenue – By all means walk on it for a few minutes because it’s famous but it’s basically just an outdoor mall with store after store and there are so many tourists.

Michigan Avenue at Night Chicago

The Skydeck at Willis Tower – This is the suspended glass box at the top of Willis Tower (formerly the Sears Tower). It honestly is really cool but the line gets SO long so fast and it is expensive. Plus, if the weather doesn’t cooperate you won’t be able to see much so you have to hope for a perfectly clear day with no fog.  For those reasons I say skip it.

Skydeck Willis Tower Chicago

Navy Pier – Your typical carnival style pier with a few rides, a ferris wheel, and overpriced hot dogs and popcorn. We went once because I had never been and it was fine but it was never worth going again.  The view of the skyline is pretty but you can get similarly great views at many better spots.

Navy Pier View of Chicago Skyline



Have you ever been to Chicago?  Any favorites that I missed?  Share them in the comments below so we can all benefit from them!


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