Exploring Chicago Neighborhoods,  museums,  music,  theatre

the perfect 3-day Chicago travel guide

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Here is my guide to help you plan the perfect 3 days in Chicago with insight from a local (born & raised) & a tour guide. It is for first-time visitors to Chicago, including solo travelers, couples & families with kids. It covers where to stay, how to get around, what to pack & what to do. I will share some tips, tools & products to help you plan & enjoy your stay and an itinerary for each of your 3-days in Chicago. I’m warning you now, 3-days won’t be enough time, but it’s a good start!

getting here

Personally, I use Expedia for last-minute deals to search for flights when I have the itch to get out of town to explore a new part of this big, beautiful world. Super easy to search for the best price for flights. They also have alert options so you can keep an eye on your flights.

where to stay

Now that you have a handle on flights, next on the list is where to stay. I would suggest either a condo rental or one of the many hotels available. Go with a condo rental if you want to experience living like a local since it will most likely be in a neighborhood. Bucktown, Wicker Park, Logan Square & West Town are all good neighborhoods to stay in where everything (cafes, restaurants & bars) is easily accessible, walkable, or a quick ‘L’ or rideshare to downtown. Hotels are a good choice because they have many locations throughout the city (& some neighborhoods) and have various amenities like gyms, pools, spas, or rooftops with spectacular views.

You could always look into a hostel if you prefer the budget route. Click here for some options.

The following hotels got high ratings from my clients for services, amenities & location: the Sofitel (quick walk to The Historic Water Tower & Magnificent Mile), Chicago Athletic Association (Cindy’s rooftop & across the street from Millennium Park), the Thompson (near Rush St & the Gold Coast neighborhood), Four Seasons (also a quick walk to The Historic Water Tower & Magnificent Mile), the Langham (right on the Chicago River & Riverwalk) & Park Hyatt (also a quick walk to The Historic Water Tower & Magnificent Mile).

how to get around

Once you have figured out your lodging, then transportation is next on the list. How does one get around a big metropolis like Chicago? Easy, you have multiple options. But make sure you bring good walking shoes (see my recommendation below) because Chicago is a walking town. Get around by walking, biking, taking public transportation, grabbing a cab (yes, we still use those occasionally), or rideshare. You should also try the water taxi, depending on the season.

No rental car is needed if you are staying in the city. Believe me, if you can avoid driving, you should. Even if you are here for a work conference in the suburbs, check with your hotel to see if you are near an ‘L’ line or the Metra train (the commuter train that gets suburbanites downtown). Hotels in the suburbs may have a shuttle.

public transportation

Here are some tips for taking public transportation (the ‘L’ or the bus). ‘L’ stands for elevated, as in the elevated train that goes above ground & traffic. There are eight lines total (Red, Blue, Brown, Green, Yellow, Purple, Orange & Pink). We call them all the ‘L’ even though some lines are elevated & some lines go underground (the subway). Interesting fact: The ‘L’ is over one hundred years old! The first line that ran to Jackson Park was a people mover, getting them to the World’s Columbian Exposition of 1893.

You can purchase a Ventra card at any CTA (Chicago Transit Authority) station, and it can be used on both the train for $2.50 & the bus for $2.25. You can get a good transfer for two additional rides within 2 hrs for a quarter. Depending on the duration of your trip, you can purchase a 1, 3, or 7-day pass, and they cost $10, $20 & $28.

Download the Ventra app. You can check your Ventra Card’s balance, add value or passes, get arrival/departure times and account alerts. You can also use the fare value from your Ventra transit accounts to buy mobile tickets for riding Metra trains as well. Also, I would suggest using the cta trip planner to get around. Plug in your starting destination and where you are going; it will give you options for different routes.

I don’t have a car for many reasons, and one of them is that Chicago is easy to get around without a car. Plus, you see the city differently on a bus, train, or bike.

You can take the ‘L’ in from either airport. Take the Orange Line from Midway or the Blue Line from O’Hare. That is if you don’t have a lot of luggage since it’s much easier to navigate if you travel light and have only one bag. Look for escalators or elevators at cta stations. If you are schlepping a lot, then a taxi or rideshare is the better choice.


We are a great theatre town with traditional holiday classics like The Nutcracker & A Christmas Carol and many more. If you are a theatre buff, click here for a great array of options. Also, check out Hot Tix for half-price tickets. My favorites are Theatre on the Lake, the Steppenwolf, and the Looking Glass Theatre (housed in the Historic Pumping station across the street from the Historic Water Tower) for their creative productions and interesting history.

Looking for dance & musical theatre? Check out what’s at the Joffrey Ballet, the Lyric Opera & the Harris Theatre! Interesting fact: Theatre on the Lake was a sanitarium for sick children back in the late 1800s/early 1900s. It was open-air, and the kids slept in hammocks. The fresh lake air was thought to cure babies suffering from tuberculosis and other diseases.

How about a magic show? I’ve heard really good things about the Chicago Magic Lounge in Andersonville. Check out Goldstar for discounts on tickets for many different experiences.

photo by Chenyu Guan – Unsplash

where to eat

Lately, I’ve been using google maps to decide where to eat. Traditionally, restaurants come and go, and sadly, many places are closed due to the current state of things. Bring it up on your phone, and it will show you what is currently open near wherever you are. I predict increased foot traffic from worker bees & tourists in the Loop, and new restaurants will rebound. Your best bet, for now, is to check google maps since it should be pretty current & accurate.

Here are my favorite lunch spots when I’m in the Loop. Cafecito, BienMeSabe, and Revival Food Hall. Revival Food Hall has the best neighborhood restaurants altogether in one spot. So many delicious options to choose from! Before everything shut down last year, food halls were a huge, new trend. I hope that they will indeed come back. Click here for the latest info on the food hall options. Here’s my BienMeSabe blog post.

Want to try a Chicago-style hot dog, pizza (thin & deep-dish), or a beef sandwich? Click here to find out where to get some iconic Chicago food staples. And here’s my advice regarding the pizza: while deep-dish can be AMAZING, take it slow. Get a pizza and a big salad to share and a nice glass of wine or local beer. Trust me here: you don’t have time for a food coma to slow you down. When I’m craving deep-dish (and I’m a thin-crust girl), my go-to is Pizzeria Uno & Due and Lou Malnati’s fresh out of the oven.

We have a lot more incredible food besides the Chicago classics. If you feel like exploring and checking out some of our 77 Chicago neighborhoods, here are some updated new & essential restaurants. For the record, when I crave Indian food, I go to Devon Avenue in Rogers Park. Mexican? Pilsen. Pho? Argyle Street. Dumplings? Chinatown. While there are some excellent restaurants (food halls!) in the Loop, you should venture out to the neighborhoods for various delicious options. Attention foodies, this just in: Michelin’s Chicago Bib Gourmands. What is a Michelin Bib Gourmand, you ask? It is quality food for good value. Didn’t I mention that we have way more than pizza, hot dogs & beef sandwiches?

best weather

The best month for Chicago weather, IMHO, is September. You still get late summer warmth, but activities are slowly winding down. The second best season is summer (June – August), where there are almost too many things to do, but that’s a good problem to have, and the weather is more moderate. But remember, the weather here is fickle, and you need layers to be prepared for your perfect 3-days in Chicago. Even in the Summer, temps can plummet, and you will feel it if you are downtown near the lake, Lake Michigan, that is. If the wind switches direction and comes in from the north, it could drop 10-15 degrees in a matter of minutes. That’s why we have so many wardrobes here! I know it sounds like an excuse to shop more, but being prepared makes a world of difference.

what to pack/wear

Chicago is very walkable, so good walking shoes are a must. Admittedly, I am a shoe freak and always on the hunt for cute & comfortable walking shoes. Being a tour guide, I’m on my feet all the time, all year round, and getting a blister or having achy feet just won’t cut it. I’ve done a lot of research for the last 10+ years, and here are my walking shoe recommendations.

For all-day tours, I recommend good supportive shoes (lol…so does my podiatrist) like Asics, Dansko, or Vionic brands. I’ve worn Asics since my running days and was hooked the moment I tried them on. They come in a variety of great colors and have a range of prices. Dansko & Vionic have many cute, supportive sandal styles when you just need a break from sneakers.

I also like Allbirds. Super cute & comfortable, and that’s not all. They are ethically & sustainably produced using wool & their shoelaces are made out of recycled plastic bottles! I’m horrified and can’t even imagine the global waste from this past year of being locked down, so every little bit helps. And they are machine washable. My go-to’s are the Tree Skippers style (Jet Black with White Sole). I have friends who swear by these for long distances, and while they are really comfortable, I wear them for short tours.

Other must-have staples are a hat, sunglasses, sunscreen, and a lightweight, packable jacket with a hood. I like hats with a small brim to keep the sun off my face. And since I’m pretty much out every day from spring through fall, this is important to me. During the thick of the summer, I usually go for a straw hat with a bigger brim for more sun protection like this one.

I am a Ray-Ban girl and always have been. I switch between two pairs. Of course, even with sunglasses and hats, I still wear sunscreen. I discovered Supergoop! Sunscreen (for face & body) last summer. It’s a hydrating, nourishing, broad-spectrum product made with natural ingredients & reef-safe. And don’t forget good deodorant! Speaking from experience, it was hard finding one that would last through an all-day tour. I’ve tried so many natural deodorants without any luck until I found Lume. It smells great, has clean ingredients & actually works! I also love their soap & deodorant wipes.

This may sound a little crazy, but I wear cashmere all year round. I have a cashmere wrap I use for traveling and a cashmere cardigan that I use as a light jacket. I just discovered Quince, an eco-friendly, reasonably priced cashmere line. It is worth a peek because they also have a great selection of high-quality natural fabrics besides cashmere and great price points.

A lightweight, packable jacket with a hood is handy for rainy days, eliminating the need for an umbrella.

Now that you are prepared, here is your perfect 3-day Chicago guide!

day #1

I suggest starting in the Loop. The Loop is the central business district in downtown Chicago. It’s close to everything: world-class public art & architecture, the Lakefront, museums, and green space, so it’s a good place to begin. Make your way to the Cultural Center, 78 E Washington St (Michigan Ave & Washington St).

If you need a coffee and/or snack, my recommendation is to walk through the alley behind the Cultural Center (notice the mural Rushmore) and make a quick left onto Randolph St to the Intelligensia Millennium Park Coffeebar. A local, homegrown company that began in 1995 with a great mission & story. And IMHO has the best coffee in the city. Now that you are all fueled up and ready for an adventure, explore the inside of the Cultural Center. Head east (toward the lake) and head into the Randolph entrance.

Here is a video tour narrated by Chicago’s favorite local historian. Click here to get the latest, updated Cultural Center events & exhibits as they become available.

Make sure that you check out both domes, the Tiffany Dome in the Bradley Preston Hall (the city’s first library) & the G.A.R. Grand Army of Republic Memorial. There are many free exhibits on various subjects, music, art, architecture, etc. that you can peruse while walking through the building. You may even be lucky enough to enjoy the free weekly classical concerts at noon. They also have bathrooms. Now, it’s time to head over to Millennium Park.

A stroll through Millennium Park includes the very popular Cloud Gate (aka the Bean), Pritzker Pavilion, Lurie Gardens, and Crown Fountain. Admire the art & architecture and enjoy some good people-watching. And don’t forget the kid-focused Maggie Daley Park right next door with a few playscapes, garden spaces, a skating ribbon, a climbing wall, and mini-golf. Here’s more stuff to do with the kiddos.

Time to jump on a Divvy bike and go check out Buckingham Fountain. Click here to read my post on Buckingham Fountain. Now, ride to the museum campus for the best view in the city. Here, all in one place, are the Shedd Aquarium, the Planetarium, and the Field Museum. If you are riding a bike, please be safe and find and use the designated bike lanes. Interesting fact: Did you know that in 1995, Lake Shore Drive was relocated to create the Museum Campus? It used to run right through the Museum Campus.

But before going to any museum, get your Go Explorer Chicago Pass to save you up to 40% off! Remember, most museums are open until 5 pm, and some have a day with extended hours, so you may want to put this on your list for earlier or later, depending on the day.

Looking for something to do in the evening? Come back to catch a concert/movie at the Pritzker Pavillion. Bring a chair/blanket, snacks/drinks, and relax under the stars.

day #2

Go on an Architectural River Cruise. There are many options to choose from: Chicago Architecture Center, Wendella, Shoreline, etc. They offer slightly different options, so you should check each company to see what best fits your style & budget. But it’s a definite must-do while in Chicago. You can schedule this any time of day, morning, noon, or night. You’ll want to keep this in mind when planning your day. Check the weather and remember it can get pretty chilly on a boat or anywhere along on the Lakefront. My favorite time to go is in the evening when the sun is setting & the city lights come on.

Check out the Riverwalk. Take a stroll down the 1.25-mile stretch on the Chicago River’s south bank to the lakefront. Go to the McCormick Bridgehouse and Chicago River Museum, grab a drink/bite, or just people-watch. While you are on the Riverwalk, don’t forget to come back at dusk to check out Art on the Mart.

Walk north up the Magnificent Mile to the Historic Water Tower. Do some high-end shopping along the way. Then, it’s time to relax, have a drink, and take in the view at the 96th Signature Lounge in the John Hancock. The Hancock is better suited for adults, while the Sears (Willis) Tower is more kid-friendly. And ladies, make sure you go check out the spectacular view from the restroom in the Hancock. Sorry guys, payback for us always having to stand in line.

day #3

Go to Lincoln Park Zoo. And while you are here, you’ll want to check out a spectacular secret garden. From the Loop, take the #151 Sheridan bus south. After a scenic bus route along the lake & through the park, it will drop you off right in front of the zoo. Use the cta trip planner to find where to catch the bus. Interesting fact: The Lincoln Park Zoo is the nation’s oldest & free zoo and started with a pair of swans.

The Chicago History Museum is not far from the zoo. Like the name says, everything you ever wanted to know and more about Chicago history. Great for all ages. Here’s my post on the CHM.

You are close to Old Town. Go check out a comedy club at either Second City or Zanies. My favorite places to eat in Old Town are Kamehachi, a sushi pioneer, Adobo Grill for exquisito Mexican, & Twin Acres, a Chicago Institution since 1932.

Since you are already on the north side, go check out a Cubs game. Get on the Brown Line at the Sedgwick stop and head north to the Belmont stop. Switch here and take the Red Line to the Addison stop. You could also take a rideshare, but be warned traffic is crazy on game day.

more ideas on what to do & see & where to go

  • Take a water taxi to Chinatown. Seriously, it is the coolest (lol … literally) way to get around the city. Besides getting a different perspective, it’s a great way to avoid the traffic. You can get an all-day pass or a ten-ride, which can be used by multiple people. Check out their routes here. Here’s my post on exploring Chinatown.
  • Go to a rooftop bar. Here are a few to get you started: Cindy’s, LondonHouse & Raised. Be warned they can get very crowded, so go early during off-hours. Here are more rooftops to check out.
  • Take a theatre tour. I used to give tours at the beautiful Chicago Theatre, the first movie palace created by Balan & Katz. The Auditorium Theatre offers a wonderful tour as well. Read all about it here.
  • Learn how to chacha/salsa/tango at parks throughout the city. Here is the SummerDance Chicago schedule.
  • Check out a farmer’s market from May through October all throughout the city & suburbs. The main market downtown in the Loop (reopening on Thursday, May 24) takes place every Thursday at Daley Plaza (the longest-running farmers market in Chicago). More markets to check out: the Green City Market near Lincoln Park Zoo, the Green City Market in the West Loop, and the Maxwell Street Market, which has a great historical past. Here are some farmer’s markets on the Northshore & in the suburbs. More farmer’s markets in surrounding neighborhoods: Rogers Park, Lincoln Square, Andersonville, Lakeview/Roscoe Village, Logan Square & Wicker Park.
  • Check out a street festival. Jump on the ‘L’ and check out one of our 77 different neighborhoods. There are so many summertime neighborhood festivals & art fairs to choose from. Here are a few of my favorites: the 57th St Art Fair in Hyde Park, Midsommarfest in Andersonville, and Maifest & Oktoberfest in Lincoln Square. Click here for the latest street festival & event info. Here’s my post on exploring Lincoln Square.
  • Catch a baseball game. Jump on the ‘L’ and head north on the Red Line to see the Cubbies play at Wrigley Field (Addison stop) or take a Wrigley Field Ballpark tour. White Sox fan? Take the Red Line to the southside to Comiskey Field (35th/Sox Park stop) or whatever they call it now. Go to Wrigley Field for the history & atmosphere. Go to Comiskey for better food & rocking music.
  • Enjoy 18 miles of lakefront, ten harbors, and 30+ beaches. Go to relax or rent a kayak. Adventurous? Try SUPing (stand-up paddleboard). It’s a blast & a great workout. There are a few rental companies to choose from. Here’s my pick.
  • Although Navy Pier is a bit touristy, it is good for families since it offers many kid-friendly attractions like the Children’s Museum, the Centennial Wheel & and the Carousel. What gets this local to Navy Pier? A Rainbow Cone, the Chicago Shakespeare Theater, spectacular views & fireworks (Wednesday & Saturday evenings from Memorial Day weekend through Labor Day weekend). You don’t have to be directly on Navy Pier to enjoy them, but somewhere south (Monroe Harbor) or on the lakefront for the best view.
  • Go Explorer Chicago Pass is a great idea if you are a museum person or traveling with kids. We have quite a few museums, and it can get pretty expensive, so click the link to save you up to 40% off! Insider tip: If you are going to the Art Institute of Chicago, you should download their app. Check out the different routes they offer based on a specific genre of art you are interested in or the amount of time you have.

If you would like someone to help guide & navigate you through the city, you could always hire me to tour you around. Go to Tours by City Girl to book a tour with me today!

I hope my perfect 3-day Chicago guide helped you plan your next trip to Chicago. Enjoy your stay and, have a memorable trip!


  • mimi

    Thanks, Krysten! Chicago loves you too! Looks like everything should be open by early July. Yay! I’m thrilled we will have Summer this year. I hope you can come to visit soon!

  • simplyjolayne

    I saw the pizza picture and it made my mouth water. Great overview. I love the details on things to see and do as well as the restaurant recommendations.

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