The Best Things to do in Chicago for First Timers’
If you’re reading this, it means you’re visiting Chicago for the first time and that is SO exciting!! There is a reason I moved here and never left. It is the best city.
Between the architecture, beaches, neighborhoods, food scene, rooftop bars and Lake Michigan, you could easily spend an entire week here and still barely scratch the surface.
As your resident local bestie, I’m going to tell you all the must-do’s, the tourist attractions, and throw in some advice while I’m at it.
Quick Facts About Visiting Chicago
Best time to visit: May–October for warm weather (summertime is a MUST); November–December for the holidays
How many days: 3–4 days for your first trip
Airports: O’Hare (ORD) and Midway (MDW)
Best neighborhoods to stay: River North, Streeterville, West Loop or just read my blog I wrote for you
Getting around: CTA, walking, rideshare and Divvy bikes
Do you need a car? No. Skip the rental car because all the parking costs add up
If you want your entire trip planned for you, you can go ahead and grab my Complete Travel Guide to Chicago. It tells you where to stay, best restaurants and bars to go to, what to do and how to book tours, what to wear, a weekend itinerary and a packing checklist. All in one place, like an email from a friend :)
1. TAKE AN ARCHITECTURE BOAT TOUR
If you’re going to book a tourist attraction, this is the one!!! I recommend it to everyone because it really is the best tour.
First, the views are literally stunning. It takes you down the Chicago River through the heart of downtown and explains the history behind all the architectural buildings along the river.
I have done this tour many times (even once in February) and it’s always packed. I would book it during sunset if you want to see even more incredible views. TIP: the best photo op will be when you get out on the lake and the city is in the background.
BOOK YOUR CHICAGO ARCHITECTURE TOUR HERE
2. SEE THE BEAN & EXPLORE MILLENNIUM PARK
This is the obvious one… go see the bean.
It’s basic but you have to get your photo op and you can’t leave Chicago without seeing it. Right next to it is Millennium Park so take a stroll through there too.
If you’re visiting in the winter time, ice skate at Maggie Daley Park!
3. WALK THE CHICAGO RIVERWALK
The Riverwalk is one of the best free things to do in Chicago and one of my favorite ways to experience downtown. Especially on a really nice night at sunset.
There are a ton of bars along the riverwalk too. And on Thursdays in the summer outside of Tiny Tapp, they have live music! It’s definitely worth checking out or just sitting on the steps and having a drink or a coffee.
4. BIKE THE LAKEFRONT TRAIL (OR JUST WALK)
Chicago has 18+ miles of lakefront trail running along Lake Michigan. You definitely don’t need to do the entire thing. Rent a Divvy bike or walk a portion of it for some of the best skyline and lake views in the city. Get your camera out and start snapping pics!!! I have so many on my phone from over the years.
But it is becoming quite a trend to walk all 18 of them lol. People also like to do a little bar crawl as there are a few bars along the trail.
5. SPEND AN AFTERNOON AT THE BEACH
One of my favorite things about Chicago is that we have a free beach! And that it’s in the middle of a city. New York meets Miami.
For a first visit, North Avenue Beach is an easy option because you’ll get one of the best skyline views in Chicago. You could also check out Oak Street Beach if you’re staying downtown.
Both are free but you can not bring any glass and at North Ave Beach, they do check your bags.
6. VISIT THE MANY AWESOME MUSEUMS
Chicago has some pretty amazing museums and exhibits. If you are visiting with kids, this is the perfect thing to do!
Located right next to Millennium Park, the Art Institute is one of Chicago’s most famous museums.
Art Institute — this is a world famous art museum for all my art lovers.
Obama Presidential Center — brand new to the city and highly recommend. But you must buy tickets in advance!
Griffin Museum of Science and Industry — a hands on science museum that is really fun. One of my faves!
The Field Museum — dinosaurs, history, and natural science.
Shedd Aquarium — this is so big and perfect indoor activity for when it’s cold!
Adler Planetarium — space exhibits and skyline views!
If you plan on going to more than 3 while you are here, I highly recommend buying the Chicago City pass which is $140 and will get you into 5 of the museums here (with the exception of the Obama Center).
7. SEE CHICAGO FROM ABOVE
There are two observation decks in Chicago to see all over Chicago up in the clouds.
Skydeck Chicago is located inside Willis Tower and has The Ledge — the glass boxes extending outside the building. In my personal opinion, it’s not totally worth it. BUT. It is included in the Chicago City Pass if you choose to purchase that.
360 CHICAGO is located on Michigan Avenue inside the John Hancock building and gives you incredible views over Lake Michigan and downtown. They also have a bar if that’s more your think! Recommend going during sunset!
You really don’t need to do both. Pick whichever experience sounds more interesting to you.
8. EAT YOUR WAY THROUGH CHICAGO
You could plan an entire Chicago trip around food. We have some of the best food in the country!!! It’s so diverse and there’s something for everyone.
For your first visit, there are a few Chicago classics you should try at least once:
Chicago-style hot dog — go to a baseball game! or any street vendor
Italian beef — Al’s Italian Beef
Deep-dish pizza — Lou Malnati’s but if you want a local’s recommendation, go to Pequod’s
Tavern-style pizza — Vito & Nicks
Chicago burger — Au Cheval is the most well-know but my favorite is Leavitt Street Inn
But don’t stop at the classics. Chicago has an incredible restaurant scene, particularly in neighborhoods like the West Loop, Logan Square and Wicker Park.
If you’d rather try several Chicago staples at once, go on a food tour:
READ MY BLOG ON BEST HAPPY HOURS IN CHICAGO
9. GO SHOPPING!
Michigan Avenue might be Chicago’s most famous shopping street, but it’s definitely not the only place to shop. And there is constantly new retailers popping up (SKIMS, Mango, Aritzia, etc)
For your first visit, you can combine a few different areas depending on what you’re looking for.
Magnificent Mile — Major retailers and luxury shopping
Wicker Park + Bucktown — Boutiques, vintage stores and larger brands around Damen, Milwaukee and North Avenue
West Loop — Trendier boutiques mixed in with restaurants and cafés
Andersonville — Independent boutiques, home stores and vintage shopping
This is another good excuse to get outside of downtown and explore Chicago’s neighborhoods.
10. VISIT THE LINCOLN PARK ZOO
Lincoln Park Zoo is completely free, making it one of the best free things to do in Chicago. It’s honestly a staple any time of the year.
Even if you don’t spend hours looking at animals, walk through the zoo and head toward the Nature Boardwalk for one of my favorite skyline views.
During the winter, they will deck it out with Christmas lights so I highly recommend checking that out too!
11. GO TO A CUBS GAME (OR WHITE SOX)
If you’re visiting during baseball season, going to a Cubs game at Wrigley Field is one of those Chicago experiences that’s fun even if you don’t particularly care about baseball. Wrigley is basically a street full of sports bars. So even if you don’t go to a game, I recommend going there to bop around on a game day.
Or you can totally switch it up and go to a White Sox game — they have some of the best food in this stadium and I always have a blast!
12. SEE A COMEDY SHOW (MY FAVE)
This is my favorite thing to do in the city and to take visitors to. Chicago has a huge comedy scene, and this is one experience that often gets overlooked on first-time Chicago itineraries. So many SNL greats started right here in Chicago at Second City.
So check out a show at The Second City in Old Town!
BOOK: Chicago Comedy Show Tickets
13. EXPLORE CHINATOWN
Take the red line (or better yet, a water taxi) to Chinatown.
Get some Chinese food at MCCB Chicago, walk around to all the shops, try a cocktail at Nine Bar or go sing karaoke at night!
14. VENTURE OUT INTO NEW NEIGHBORHOODS
My biggest piece of advice for anyone visiting Chicago for the first time is simple: leave downtown!
The Loop and River North are great for sightseeing, but Chicago’s neighborhoods are what makes Chicago who it is. There are SO many different vibes throughout the city and it’s always worth checking out.
Depending on your vibe, check out:
Wicker Park + Bucktown — Vintage shops, restaurants and nightlife
Logan Square — Restaurants, cocktail bars and a more local neighborhood feel
Lincoln Park — Pretty streets, lakefront and restaurants, families
West Loop — Food and nightlife
Old Town — Comedy, bars and historic Chicago
Lakeview + Wrigleyville — Sports and nightlife
Andersonville — Independent shops, restaurants and neighborhood charm
Not sure which area makes sense for your trip?
→ READ MY BLOG ON WHERE TO STAY IN CHICAGO
16. TAKE THE GHOST & GANGSTERS TOUR
I think this is one of the best tours Chicago has to offer. This guided tour, given by locals who are often comedians, is a walking tour taking you through all the infamous spots where gangsters and ghosts haunted the city.
It was so much fun and I learned a ton about the tragic events that took place in Chicago — did I mention there was a serial killer?
You’ll just have to take the tour to find out yourself. I have a discount code!! Use AMBER5 to get $5 off your booking here.
17. GRANT PARK & BUCKINGHAM FOUNTAIN
If you go to Lolla, you’ve been in Grant Park. But an iconic photo spot is the Buckingham Fountain.
This is one of the largest fountains in the world!
18. SIP A DRINK ON A ROOFTOP
If you’re visiting when the weather is remotely cooperative, you need at least one rooftop drink. There are so many great rooftops around the city!
Chicago has rooftops overlooking the river, Lake Michigan and the skyline.
Instead of making this post 900 years long, I already put together an entire guide:
→ BEST ROOFTOP BARS IN CHICAGO
shop all my favorite travel essentials
Best Time to Visit Chicago
There really isn’t one best time to visit Chicago — it depends on what you want to do.
May–June: Warmer weather without peak summer crowds
July–August: Beaches, patios, rooftops, festivals and peak Chicago summer (you have definitely heard of summertime chi)
September–October: Cooler weather, fall activities and generally great walking weather (but also could snow in October)
November–December: Holiday markets, Christmas decorations and festive activities but cold AF!
I hope you have the time of your life in my favorite city in the US!!
