Chicago 4 Day Itinerary: Best Things to Do, See & Eat
Planning the perfect Chicago 4 day itinerary can feel overwhelming with so many iconic spots to explore.
I was born in the Windy City and made my way back to spend a good chunk of my 20s here as well, so you can trust my guidance when I tell you how to spend 4 days in Chicago.
I’ve curated this guide to help you experience the best of the Windy City like a true local. From deep-dish pizza to hidden speakeasies, I’ll show you how to make the most of your time in Chicago while avoiding tourist traps.
Chicago 4 Day Itinerary: Quick View
Here’s your day-by-day snapshot of how to experience Chicago’s highlights while diving into its vibrant neighborhoods:
Day 1: Downtown Chicago’s Greatest Hits
Day 2: River Views & Comedy
Day 3: Cultural Neighborhoods
Day 4: Local Favorites & Art
Chicago 4 Day Itinerary: Full View
Let’s break down each day to help you navigate the city efficiently while experiencing both iconic attractions and local gems.
Day 1: Downtown Icons, Michigan Avenue & Hidden Gems in the West Loop
Lunch at Portillo’s
Start your Chicago journey properly at Portillo’s (100 W Ontario St ). Here you can try two Chicago classics under one roof – the Chicago style hot dog and an Italian beef sandwich.
Remember, no ketchup on a Chicago dog. And if you get the Italian beef, order it dipped with hot giardiniera peppers if you’re brave.
Whatever you do, don’t skip the chocolate cake shake. It’s exactly what it sounds like – an entire slice of their famous chocolate cake blended into a milkshake. Is it excessive? Absolutely. Will you regret it? Well, your tastebuds certainly won’t.
Window shop along the ‘Magnificent Mile’
After that hearty lunch, you’ll appreciate this walk along Michigan Avenue. But here’s a tip – while others rush from store to store, take time to look up.
The architecture along this stretch tells Chicago’s story better than any guidebook.
Check out Millennium Park
Sure, everyone snaps a photo at The Bean (officially called Cloud Gate), but there’s so much more to discover here. Time your visit to Crown Fountain when the faces are “spitting” water.
In summer, catch a free concert at Pritzker Pavilion where locals spread out picnic blankets and uncork wine as the sun sets behind the skyline.
You should also take some time to cross the winding BP Bridge to Maggie Daley Park. The view back toward the city makes for a great photo spot.
Drink with a view at Cindy’s Rooftop
Next, skip the tourist hot-spot Navy Pier and head to one of my favorite rooftops in the city.
Cindy’s, perched atop the Chicago Athletic Association Hotel, feels like stepping into Chicago’s glamorous past with thoroughly modern cocktails.
The view over Millennium Park is unbeatable, and if you time it right, you’ll watch the city transform from day to night.
With cocktail names like “No Soup For You” and “Schmoke & A Pancake,” you know you are in for a good time.
Don’t drink? No problem. A friend who was visiting me from out of town was the one who pointed this out to me – Chicago has an enviable mocktail scene. Cindy’s is no exception.
Recharge for dinner
Head back to your hotel for a quick refresh – trust me, you’ll want to look sharp for what’s coming next.
The West Loop, particularly Fulton Market, has transformed from Chicago’s meatpacking district into our hottest dining destination.
One of my favorites in the area is Aba (302 N Green St), where the Mediterranean-inspired dishes are served in what feels like an indoor garden oasis.
If you can snag a reservation, Duck Duck Goat is another top choice in the area. Chef/Owner Stephanie Izard’s creative Chinese dishes never disappoint.
For Italian, book a table at Monteverde. There are plenty of top-notch restaurants in the area so see where you’re able to get a reservation during your travel dates and enjoy a delicious evening out.
Nightcap at a speakeasy
After dinner, head to this unassuming speakeasy: The Blind Barber (948 W Fulton Market) is exactly what it sounds like during the day – a functioning barbershop.
But push through the back door at night, and you’ll discover one of Chicago’s coolest hidden bars.
The contrast between the bright barber shop facade and the moody, intimate bar space behind it is pure Chicago magic.
Order their signature Hot Heather cocktail and settle into one of the vintage leather couches. It’s the perfect spot to digest both your dinner and your first day in the city.
But be aware, it can be a bit loud in here some nights when they have a DJ present.
Day 2: Lakefront Luxury, River Views & Chicago’s Comedy Legacy
Brunch on the beach
Start your day at Shore Club (1603 N Lake Shore Drive), if you are visiting after May. The Mediterranean-inspired brunch menu is fantastic, but it’s the setting that steals the show.
Their covered patio serves uninterrupted views of North Avenue Beach and the glittering Lake Michigan. The last time I was there a friend and I split the Mykonos board – it was so yummy!
After brunch, kick off your shoes and take a stroll along the beach – watching the joggers, volleyball players, and sailboats against the backdrop of Chicago’s skyline really never gets old.
Architecture cruise
This “tourist attraction” is actually one of my favorite things to do in Chicago. This 90-minute river cruise provides history and details to help you better understand the stories behind the beautiful buildings around the city.
You’ll see top highlights while sidestepping street traffic when you take to the water. It’s such a leisurely and fun way to spend some time getting to know this pretty city.
Riverwalk sips
After your cruise, don’t rush off – the Chicago Riverwalk is one of the city’s best recent additions. During summer months, it’s a great place to people-watch while sipping wine at City Winery’s riverside outpost.
Time your visit right, and you can catch Art on the MART after sunset – it’s the largest permanent digital art projection in the world, transforming the entire facade of the Merchandise Mart into a canvas.
Dig into some deep dish
Look, as a local, I have to tell you – deep dish is more of a special occasion pizza than an everyday thing for us. But when we do indulge, we do it right.
Head to the original Pizzeria Uno (29 E Ohio St) where it all began in 1943. Order immediately when you sit down – these beauties take 45 minutes to prepare.
Another personal favorite place to get Chicago style pizza is Giordano’s for their perfect cheese pull and massive slices.
Whatever you choose, don’t plan on moving much immediately afterward – this pizza can really weigh you down. Remember to hydrate!
Sunset cocktails with a view
Time to elevate your evening – literally. The Signature Room on the 95th floor of 875 N Michigan offers the best views in the city (even the women’s bathroom has the most incredible city vista – seriously!).
For something more contemporary, LH Rooftop at LondonHouse serves craft cocktails alongside perfect skyline views.
If you’re heading to Second City later, make your way to the nearby J. Parker atop Hotel Lincoln – their glass-enclosed rooftop offers stunning park and lake views in any weather.
Comedy show at Second City
End your night where countless comedy legends got their start. Second City’s 8pm show is Chicago entertainment at its finest – sharp, witty, and distinctly Midwestern.
I’ve seen countless shows here, and they never fail to highlight why Chicago’s comedy scene is unmatched. Who knows? You might be watching the next Tina Fey or Steve Carell.
Day 3: Cultural Discoveries, Local Art & Chicago’s Best Hidden Neighborhoods
A morning in Chinatown
Skip the hotel breakfast – we’re starting today at Saint Anna Bakery, where the aroma of fresh custard buns will make you glad you made the trip south.
Grab a coffee at Tous Les Jours, then explore Chinatown Square Plaza. The zodiac sculptures aren’t just photo ops – find your sign and read about your fortune.
Peek into Ichiban for unique snacks you won’t find anywhere else in the city – the perfect souvenirs that actually fit in your suitcase.
Lunch in Pilsen
Next, head to one of the top food neighborhoods in Chicago. The squash blossom tacos at Rubi’s are tasty. I have my own sights (and stomach) set on QuesaBirria Jalisco Tacos the next time I’m in the area.
18th Street Art Walk
Time Out has named this one of the world’s coolest streets, so it’s definitely worth scoping out for yourself when you’re in the area.
The murals here aren’t just Instagram backgrounds – they tell stories of culture, community and celebration.
National Museum of Mexican Art
After visiting myself last summer, I feel this museum should be required viewing for locals and visitors alike.
Every exhibit I’ve seen here has been thoughtfully curated and powerful. Take your time – the gift shop is also one of the best places to find unique, locally made art pieces.
Dinner at Spacca Napoli
We’re heading north to my favorite pizza place in the city – and no, it’s not deep dish.
Spacca Napoli (1769 W Sunnyside Ave) serves the kind of Neapolitan pizza that you expect to get in Naples itself. And if their burrata is on offer, it’s a must-order – it’s imported from Puglia and is divine!
If you’re looking for something to satisfy your sweet tooth afterwards, stop at Margie’s Candies. This place hasn’t changed much since 1921 and even the Beatles visited here after their Chicago concert.
If you have the energy for more, cap off your night at Sleeping Village for great local bands, craft beers and zero pretenses.
Day 4: Local Favorites, Arts & Culture, Hidden Gems
Active start on the 606
Chicago’s answer to NYC’s High Line, The 606 is where you’ll find locals starting their day off right. This elevated trail, built on old railway lines, gives you a unique perspective of the city’s northwest neighborhoods.
Join the morning joggers, walkers and cyclists or take it slower and stop at the various lookout points.
For breakfast, something truly special – Kasama (1001 N Winchester Ave). This Filipino-American restaurant earned a Michelin star for their dinner service, but has also become very popular for its daytime offerings.
Here’s the insider move: arrive before 9am or order online to avoid the inevitable lines. Get the breakfast sandwich and some pastries to try, too.
Art Institute
If you have time and are not departing today, then don’t miss the Art Institute. You could easily spend hours and hours here, but to keep the overwhelm at bay skip the main entrance crowds and use the Modern Wing entrance on Monroe Street.
Spend an hour or so taking in the modern art exhibit and maybe stop into the gift shop for a Chicago souvenir before heading to your next stop.
Try the original brownie
Here’s a piece of sweet history: the brownie was invented in Chicago for the 1893 World’s Fair!
Head to the Palmer House Hilton for their original recipe brownie. The gorgeous ceiling inside alone is worth the visit.
Pick up Garrett’s popcorn
Listen, there’s a reason why you’ll spot locals at O’Hare with bags of Garrett’s Popcorn – it’s a classic.
Head to the Michigan Avenue location for the famous Chicago Mix (now officially called “Garrett Mix” – caramel and cheese popcorn mixed together). This also makes a great gift!
Evening in Andersonville
For your final dinner, make your way to yet another Chicago neighborhood. Andersonville feels like a small Swedish town dropped into the city’s north side.
While you’re in the area, check out the Galleria market for local goods that make unique souvenirs.
Especially if you’re a beer lover, go to Hopleaf – a Belgian beer bar. Try the mussels steamed in witbier with frites, and take your pick from their encyclopedic beer list.
If You Have More Time…
With even more time in your Chicago itinerary, and depending on the time of year when you’re visiting, here are some additional ideas of things to do. Or, swaps to make to the itinerary above:
– Experience the TILT at 360 Chicago for thrill-seekers
– Catch a Cubs game at Wrigley Field (April-September)
– Listen to live jazz music at Green Mill Cocktail Lounge
– Visit Lincoln Park Zoo (free admission year-round)
– Take a food and walking tour
Where to Stay in Chicago
Choose your base carefully to maximize your Chicago experience. Alternatively, if you’re up for a bit of a commute into the city consider a more affordable hotel outside of Chicago:
🏨 Luxury: The Peninsula Chicago
Prime Magnificent Mile location with a world-class spa and rooftop views, The Peninsula Chicago offers the height of luxury and their afternoon tea is a classic favorite.
👉 Check prices and availability
🏨 Mid-Range: Thompson Chicago
The Thompson Chicago is a stylish Gold Coast hotel within walking distance to both downtown and local neighborhoods. Great value for location and amenities.
👉 Check prices and availability
🏨 Budget: Arlo Hotel
Millennium Park-adjacent Arlo Hotel offers modern rooms and historic architecture. Perfect location for first-time visitors.
👉 Check prices and availability
Insider Tips from a Native & Local Chicagoan
Here are some additional Chicago travel tips to keep in mind as you plan your visit:
- Skip Navy Pier unless you’re visiting with young children
- A city pass is worth it if you’re planning to visit 3+ major attractions
- Use Divvy bikes as an affordable way to get around if you’re comfortable
- Chicago winters can be tough – pack accordingly November through March
- Restaurant reservations are essential Thursday through Sunday, but at the most popular restaurants it’s smart to have one any day of week
- Download the Ventra app for easy public transit navigation
- Like with any big city, stay safe in Chicago by being aware of your surroundings and possessions at all times
You might also be wondering…
As you plan your Chicago travel itinerary, be aware:
Is 4 days enough for Chicago?
Four days allows you to experience downtown highlights while exploring 2-3 neighborhoods thoroughly. It’s ideal for first-time visitors.
What is the best month to go to Chicago?
September and early October offer perfect weather and smaller crowds. May-June are also excellent with festivals beginning and comfortable temperatures.
Do you need a car to see Chicago?
No – public transit and rideshare services can get you everywhere in this itinerary. Parking is expensive and often difficult to find. Personally, I find driving in Chicago stressful but I’m someone who doesn’t enjoy driving in general!
Final Thoughts on Your Chicago 4 Day Itinerary
Chicago offers a perfect blend of world-class attractions and authentic neighborhood experiences.
This itinerary sets you up to experience both while avoiding tourist traps. Remember to stay flexible – sometimes the best Chicago moments happen when you wander off the beaten path and discover your own favorite spots in the city.
