A Detailed First-Timer’s Guide To Chicago

July 4, 2021

It’s insane that until a few years ago, I’d never been to Chicago.  I KNOW!  But I’ve fixed that big time, with probably 10 visits over 3 years (largely for work).

And over that time I’ve completely fallen in love with the city…its architecture, history, food, waterfront trails, rooftop views, and so much more!  So I wanted to share a detailed guide for first-timers looking to get the most out of a visit to the Windy City…things to do in Chicago, where to stay, some of my favorite restaurants, and much more.

A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City!

Other Chicago adventures for your enjoyment!

Why The Chicago Architecture Foundation River Cruise Is A Must-Do

Chicago Guide:  Where to Eat & Drink

Foodie Heaven: A Visit To Chicago’s Time Out Market

Visiting The World’s Largest Starbuck’s: The Chicago Roastery

Hiking In Starved Rock State Park, A Perfect Chicago Day Trip

I rarely get a good view of the city when I fly in or out, but I’ve managed to snag a couple!

The view flying into Chicago...never gets old!

How this post is laid out

  • General tips for visiting Chicago
  • Where to stay in Chicago
  • Things to do in Chicago (the majority of the post)

General tips for visiting Chicago

Weather is always one of the biggest things to take into consideration when planning a trip to Chicago.  I think the city is great year-round, though if there are 4 feet of snow on the ground then I’ll take a pass.  I truly hate cold.  But several of my visits have been in December/January (including during a Polar Vortex) and I survived.

I personally think late spring and through the summer are great, so if you had to choose then I’d say late May through September are perfect.  I’m partial to late June.  I’ve also heard it’s gorgeous in the fall when the leaves change, but it’s one of the few times I haven’t been able to experience.

The weather in Chicago is prone to extremes and quite capricious…you can experience multiple seasons in a day and it can change in an instant.  The wind also amplifies the temps, particularly cold.  I recommend being prepared with layers and have an umbrella or light rain jacket at all times.

It’s not uncommon for dense fog to roll in unexpectedly as well, so just make sure to take weather into account when planning anything that is view-dependent (rooftop bar, observation deck, architecture river cruise, etc.).

I had to share this snapshot from one of my trips…first I was confused, and then (literally) LOL’d.  Come on, Chicago…lock it up.

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How to get around

Chicago is a SUPER walkable city, so if you’re mostly concentrated in the downtown area and surroundings then I definitely recommend walking as much as possible.

If the weather is gross or you need to get somewhere further, there are plenty of cabs and Ubers/Lyfts.  The city has a great public transportation system as well including the train (“the L”) and buses.

I’m usually lazy and take a cab from the airport (both Midway and O’Hare) to downtown, though to be fair I’m usually on a work trip.  But I have taken the L to the airport as well during rush hour and it was really easy and faster than sitting in traffic.

The Windy City is very walkable

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Where to stay

I almost always stay in the River North/downtown area, and have tried a number of different hotels.  There are lots of great options and usually you can find pretty affordable nightly rates.

On random rare occasions I’ve happened to visit when something major was going on in the city (a massive convention, etc.) and there wasn’t much available, but this is very rare.  I will say that the major spike in travel as COVID restrictions eased has put some pressure on hotel prices, though, so I would book ahead.

I’ve stayed most frequently at Hotel Chicago Downtown (right on the river), The Godfrey, Marriott Magnificent Mile, theWit, and the Hyatt Regency.  When I’m not traveling for work, I always find the best options and deals on Booking.com.  While I’m usually a big fan of rentals like Airbnb, I haven’t had much luck with that in downtown Chicago.

For something unique and historic but still reasonably affordable, consider Chicago Athletic Association (wow!!), Club Quarters on Wacker (similar views to London House), or stayPineapple which is in a beautifully renovated historic building.  Obviously there are some amazing splurge hotels in the area as well, like The Langham and Kimpton.

Where to stay in Chicago & more in this detailed city guide

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What to do in Chicago

Now that we’ve got that out of the way, I’ll share some of my favorite things to do in Chicago below.  A lot of this is focused in the main downtown area or fairly close, and you should be able to walk most places.

I’ll give my usual caveat here that I’m not really a museum person, so if you’re looking for museum tips you won’t find that here…but there are many amazing ones in Chicago and you definitely should check them out!

The Riverwalk

The Riverwalk is my one true love in Chicago, and a major part of local life!  Sunrise, daytime, sunset, or night…the amazing architecture and just serious VIBE are worth your time.

A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City! #chicago #illinois #ustravel #windycity #cityguide

Things to do in Chicago for first-timers - spend time on the Riverwalk

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Besides just strolling along and enjoying the ambiance, there are a number of bars and restaurants along the Riverwalk, many with great outdoor seating (like the always-packed City Winery).

You can rent kayaks, go for a run, catch a river cruise, visit the Bridgehouse & River Museum, go fishing (with a license!) or birdwatching, and much more.

Things to do in Chicago for first-timers - spend time on the Riverwalk & stop for a glass of wine

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Catch sunrise at the lakefront or on the Riverwalk

I often like the less-crowded times on the Riverwalk when it feels like I have it all to myself.  Early mornings and sunrise (especially along or running toward the lakefront) and sunset (which isn’t often spectacular but still has a peaceful vibe) are great times to visit, as well as at night when the lit-up buildings reflect on the water.

When I’m in Chicago for work, my favorite thing when it’s not insanely cold is to go for a run along the Riverwalk, then stop at Beatrix on my way back to the hotel for a giant latte and a morning bun.  Or Big Shoulders for iced coffee and Firecakes for donuts 🙂

Things to do in Chicago for first-timers - sunrise on the Riverwalk

Things to do in Chicago for first-timers - sunrise on the lakefront is amazing

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Soak in all the amazing architecture

The city has an insanely impressive architecture history, and exploring it is one of my favorite things to do in Chicago.  The late 1800s in particular were a whirlwind of creation that became a foundational piece of American architecture style.  This was somewhat enabled by the fact that Chicago largely burned down in 1871, providing a blank canvas to work with.

From architect William Le Baron Jenney who became known as the “Father of the American Skyscraper”, to the famous Daniel Burnham and Louis Sullivan (of “Devil in the White City” fame), to Frank Lloyd Wright, there are dozens of gorgeous historic buildings and different architectural styles to soak in.

A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City! #chicago #illinois #ustravel #windycity #cityguide

Things to do in Chicago for first-timers - appreciate the varied & historic architecture

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Enjoy the quirky details as well…both visual and from a storytelling standpoint.  One of my favorite buildings in Chicago is Tribune Tower, a gorgeous neo-Gothic spire that’s impossible to miss along the riverfront.  Not only is the overall style and detailing beautiful, but if you look closely you’ll see lots of seemingly-random bits and bobs stuck in the walls.

Embedded in the façade are 150+ fragments of stones from famous sites around the world.  The unique collection started when a journalist covering WWI in Belgium took a piece of the ruins of Ypres Cathedral home with him as a memorial, and now there are pieces of everything from the Taj Mahal to Wrigley Field to the Great Pyramid at Giza.

Supposedly they’re all obtained by “honorable means”, but it’s earned the building the affectionate local nickname of the “Thievery Building”.

Things to do in Chicago for first-timers - appreciate the varied & historic architecture

And don’t only marvel at the outside of buildings…the inside is sometimes just as impressive.  On a recent visit I paid a visit to the Rookery, designed by Burnham and Root.

It was one of the tallest buildings in the world when it opened, but is now known more for its beautiful Romanesque red granite entrance arch and a fascinating Frank Lloyd Wright-designed lobby.

Another example of a gorgeous building you can go in and see is the Chicago Athletic Association (now a hotel which also contains Cindy’s Rooftop)…it’s stunning inside!

Things to do in Chicago for first-timers - appreciate the varied & historic architecture (The Rookery)

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When it comes to soaking in architecture, I particularly enjoy capturing the reflections in the glass skyscrapers…buildings within buildings, the sky reflected back at you.  It’s one of my favorite things 🙂

A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City! #chicago #illinois #ustravel #windycity #cityguide

Things to do in Chicago for first-timers - a detailed guide to the Windy City

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Go on the Chicago Architecture Foundation river cruise

In my experience if you ask Chicago locals what to do when you visit, the Chicago Architecture Foundation river cruise is the ONE “touristy” thing that they will all say is a must (and something they love to do themselves).

As I mentioned above, Chicago’s architecture and history is amazing, and the river cruise is a great way to gain a better appreciation of it, and see portions you might not have experienced otherwise.  There are multiple cruises but I strongly recommend doing the official one offered by the Chicago Architecture Foundation Center.

Read a deeper post about the Architecture Foundation river cruise experience!

Things to do in Chicago for first-timers - take the Chicago Architecture River Cruise

A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City! #chicago #illinois #ustravel #windycity #cityguide

As you might expect, weather makes a HUGE difference in this experience, and Chicago’s weather is sometimes hard to predict (for instance, fog can just roll in with little warning).  The cruise will be canceled if the weather is bad, but likely may still run even if it’s foggy, so you kind of have to hedge your bets on whether to purchase far ahead or try the day of/before your visit.

Tickets cost around $50 per person (plus Ticketmaster fees) and the tour is 90 minutes long; see the official website.  Make sure you dress appropriately (it can get chilly on the water) and bring sunscreen!

Fun fact: The Chicago Architecture Foundation offers 90 different tours in Chicago!

A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City! #chicago #illinois #ustravel #windycity #cityguide

Things to do in Chicago for first-timers - take the Chicago Architecture Foundation river cruise

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Make sure to enjoy the city at night

SIGHHHHH I love Chicago at night, particularly along the Riverwalk or lakefront.  Seeing the beautiful buildings lit up in all sorts of colors and reflecting off the water is magical.

A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City! #chicago #illinois #ustravel #windycity #cityguide

What to do in Chicago - make sure to spend some time on the Riverwalk at night

Things to do in Chicago - explore the city at night, including the Riverwalk

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Go for a stroll along the Riverwalk, sit out on a patio for a drink, or head over to one of the cool food and nightlife neighborhoods like Lincoln Park, Fulton Market, or Logan Square.

Even in winter Chicago sparkles

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Reflect on (in) the Bean at Millennial Park

A.k.a. Cloud Gate, which is honestly a badass name.  The Bean is one of the most iconic, recognizable Chicago landmarks, and a must-visit despite being thronged by tourists.  Perched just inside Millennial Park and an easy walk from the riverfront, the mirrored sculpture reflects and distorts everything around it.

The park is free to visit, and you don’t have to spend much time here.  Normally you can walk right up to (and under) the Bean but during COVID they closed off a little area around it; my assumption is they’ll reopen it at some point (you can check here).  I’ve got pics of both below as each has pros and cons, and either way you can get awesome photos.

Things to do in Chicago for first-timers - you can't miss the Bean in Millennium Park

Things to do in Chicago for first-timers - you can't miss the Bean in Millennium Park

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But don’t stop there!  See the other connected parks…

So I had NEVER known until my most recent visit that the Bean is only one little part of a larger network of parks!

First you’ve got the Frank Gehry-designed Jay Pritzker pavilion, and awesome outdoor concert space right next to the Bean.  Then out front along the street is the interactive Crown Fountain (which, if I’m being honest, I find a little creepy when the faces are showing up).

Things to do in Chicago - explore Pritzker Pavilion & the other parks connected to Millennium Park

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Then one of my favorite things in this complex is the lovely small Lurie Gardens just a few steps away, a botanical garden right here in the heart of the city.  It’s just a peaceful little oasis away from the hustle and bustle (and free!).

A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City! #chicago #illinois #ustravel #windycity #cityguide

Things to do in Chicago - explore Lurie Garden & the other parks connected to Millennium Park

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EAT ALL THE THINGS!!!

I have done a MUCH deeper guide on where to eat and drink in Chicago, that I’ll continue adding to over time, but the bottom line is that Chicago’s food scene is THE BOMB.

I recommend having at least one splurge-y dinner (that doesn’t mean it has to be super expensive, more about getting reservations at one of the high-demand places).  A few of my favorites so far are Duck Duck Goat (and honestly any “Goat” restaurant you can get into), Beatnik on the River, The Purple Pig, Cindy’s Rooftop, Bar Siena, and Prime & Provisions.

LOL and that’s just the short list of faves!

Things to do in Chicago - eat all the things! I recommend Duck Duck Goat

Things to do in Chicago - eat all the things!

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It’s not all about the fancy meals either.  Amazing cocktails, craft beer, artisan ice cream, local donuts, delicious authentic Mexican street food…I mean I could go on and on about the different things you have to try in Chicago.

First off, the abundance of great local donut shops and coffee shops is one of my favorite things to explore.  When I visit for work I go for an early run on the river and then indulge in donuts or pastries and coffee.  Hit up a local brewery or City Winery, or try out a great cocktail bar (Logan Square is jam-packed with them).

Basically, if you come here and simply eat and drink your way through Chicago, I’d consider the visit a success!

Things to do in Chicago - eat and drink your way through the Windy City!

One thing you could consider, especially if you’re short on time and want to try lots of options, is a trip to Time Out Market.  This is a food hall concept that’s popped up in a handful of cities around the world (I’ve also been to the Lisbon one) and brings together dozens of the hottest, most in-demand chefs and food concepts in the city.

Chicago’s Time Out has 18 restaurants, a secret speakeasy, a rooftop bar, and a couple other regular bars, and more.  We couldn’t try everything, but some of my faves were The Purple Pig, John Manion, Mini Mott, and Abe Conlon.

Read more about our visit to Chicago’s Time Out Market here!

Things to do in Chicago - eat all the things! Time Out Market lets you sample lots of restaurants

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Walk the lakefront trail

The 18-mile-long path along Lake Michigan offers great views of the city skyline and the lake, and many opportunities for activity.  Whether you want to walk, run, bike, Segway, or just sit, exploring a small portion of the trail is a must if the weather is nice.

I haven’t experienced all 18 miles yet, so can’t say with certainty which parts are the best, but so far the easiest portion to get to in my opinion is the stretch that starts at the Riverwalk where Navy Pier sits and then curves up north.  Additionally, the views and vibe from further south by Adler Planetarium are amazing…more on that in a few minutes.

The path is flat and smooth, very easy to navigate, though it can be a little intense on windy days.  Some crazy people even surf in the lake during some parts of the year!!!

Things to do in Chicago - the skyline view from Adler Planetarium is amazing!

Swing past Navy Pier if you’re in the neighborhood

I definitely wouldn’t go out of your way, but if you’re headed to the lakefront from the Riverwalk, a quick walk around Navy Pier is nice.  I wouldn’t spend any time here, but the views are fun.

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Find yourself a rooftop bar

Rooftop culture is a major thing in Chicago, and you can see why!  Everywhere you look there’s a new angle on the city…and it doesn’t have to cost more than a cocktail.

I spent a lovely hour with a cocktail at Cindy’s Rooftop, in the beautiful and historic Chicago Athletic Association hotel (reservations recommended if you want to eat).  It looks out over the Bean and Millennial Park, and toward the lakefront.  I’m dying to try out London House as well.

Obviously weather plays a huge role in this, so summertime is the best though some of the most well-known rooftops are open year-round with heaters.

Things to do in Chicago - If the weather is nice, get to a rooftop bar!

Go a step further for a 96th-floor view & cocktail

Chicago has two different skyscrapers with observation decks, Skydeck at Willis Tower (103rd floor, has a glass ledge) and 360 Chicago (94th floor, previously John Hancock building).  Prices for the observation decks are around $30 regularly, though they offer various more expensive “fast pass” or early access options.

I actually haven’t done either, but instead did a well-known “cheat” and went to the Signature Lounge on the 95th and 96th floors of the former John Hancock Center.  We didn’t have a reservation and were just going for a drink (it’s a one drink-per-person minimum), but got there at a perfect time so didn’t have to wait in line too long.

The views are amazing, and I highly recommend this for sunset if you can catch it…and it goes without saying, but on a clear day!  Pro tip, the restaurant does have a formal dress code, though the cocktail portion doesn’t to my knowledge.

Locals will tell you that the best view in Chicago can be seen from a women’s bathroom…and they’re not lyin’!

Things to do in Chicago - the Signature Lounge is a great way to get a 96th floor view for the price of a cocktail

A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City!

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Capture that iconic Chicago view at the Adler Planetarium

Speaking of views, this was a newer find for me, but locals are well aware.  One of the best places to get an iconic look at the Chicago skyline is from Adler Planetarium.  I’d love to experience it at night sometime (or, like, on 4th of July for fireworks), but on this stunning blue-skied May morning I fell in love.

It’s a bit further out but can be walked or biked to on the lakefront trail, or you can snag a cab or bus.  Basically, if you’re exploring the Millennium Park area and then keep going south past Buckingham Fountain, you’ll hit Grant Park and then just south are the aquarium and planetarium.

What to do in Chicago - the Adler Planetarium offers the iconic Chicago skyline view

Find some secret art

Chicago’s got something for art lovers of all kinds.  In addition to world-class art museums, historic architecture, galleries, outdoor modern art, and a vibrant street art culture, there are a few public installations by famous artists hiding in plain sight.

We’ve already covered Cloud Gate and Crown Fountain, but did you know there’s a giant Picasso sculpture just chillin’ in a random plaza??  Yep, that’s right (well, it’s Daley Plaza but to me that’s random).  Not to mention a colorful Chagall mosaic (called “Four Seasons”) hanging out at the base of Chase Tower, and much more.  This list covers some of the most famous ones.

What to do in Chicago - seek out art by famous artists, like this Picasso just sitting in Daley Plaza

What to do in Chicago - it's a great city for art lovers

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See some live music

This tends to be on my list in most places, but a big city like Chicago has any kind of music experience you can imagine, and they’re a great way to really get a feel for the place.  Whether you see an intimate acoustic show at City Winery, an outdoor summertime concert at Pritzker Pavilion, or a live jam on a brewery patio, you’re living Chicago like a local.

One thing that is super high on my list is to spend some time exploring Chicago’s jazz clubs…the city has a fascinating history with jazz (and the Mob) and I’d love to immerse myself in that (here are a few thought-starters).  Sketch comedy is also a thriving scene in Chicago you should check out if that’s your bag.

What to do in Chicago - see some live music or comedy

Have a cocktail at the world’s largest Starbucks

This is a pretty touristy option but we definitely still had fun.  On one of my wintertime visits we were trying to figure out what to do on a cold, snowy winter night after a big dinner, and decided to try out the new (at the time) Starbucks Roastery.  At 35,000 feet, this Chicago store is Starbucks’ largest in the WORLD.

It spans five floors, with interesting coffee, cocktails, some food offerings, and more.  We went straight to the bar area on the 4th floor (there is a rooftop as well, in summer) and were really intrigued by the cocktail list.  The cocktails were delish and we tried the whiskey-barrel cold brew…WOWZA, so good!

The centerpiece of the entire building is a 56-foot “cask” with copper tubes that allows the beans to rest after roasting, and moves the beans between floors.  It spans the center of the building and is really beautiful and unique.

Read more about visiting Starbucks Roastery here!

Things to do in Chicago - visit the world's largest Starbucks for a cocktail

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Get out into the neighborhoods

This isn’t something people can typically do in their first visit or two, but one of the great things to do in Chicago is going further afield than just the River North and Lakefront areas.

Cool down with some Mario’s Italian Lemonade in Little Italy, head out to Logan Square for an awesome dinner and some cool cocktails, visit the (free) Lincoln Park Zoo, find a patio and enjoy the art and history in Oak Park, soak in the history and art in Bronzeville…basically, once you’ve done a good job exploring the downtown area, get further out!

Things to do in Chicago - get out into the neighborhoods and explore

Things to do in Chicago - get out into the neighborhoods and explore

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Take a day trip out to Starved Rock

And if you REALLY have some time in the city and want to get some legit hiking in, you can drive out to Starved Rock State Park for some nature.

Less than 100 miles from downtown Chicago, the park feels like another world.  It’s an oasis of towering trees, (seasonal) waterfalls, tons of different winding trails and wooden staircases, beautiful views, and more.  It was too dry for waterfalls when we were there mid-summer, but gorgeous nonetheless.

Pro tip:  After burning all those calories, stop at Tangled Roots Brewing Company in nearby Utica for delicious food and flights of local beer

Read more about our Starved Rock State Park adventure!

If you have time, take a day trip to Starved Rock State Park for some hiking - things to do in Chicago

And there you have it…a super detailed guide of things to do in Chicago, whether you have just a day to explore or an entire week to really immerse yourself in this amazing city!  Hit me up with any questions and I’ll do my best to answer them in the comments!

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A Detailed First-Timer's Guide to Chicago | If you're planning a trip to Chicago (Illinois, USA), this super in-depth post of what to do in Chicago, where to stay, places to eat & drink, & more tips has got you covered. How to plan the best trip to Chicago, Chicago hotel recommendations, US travel tips. Chicago travel tips for the Windy City!

Comments (1)

  • Lauren

    July 6, 2021 at 4:19 pm

    The walk along Lake Michigan sounds amazing – didn’t realise it was 18 miles long! Look forward to visiting Chicago in the future.

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