Looking for the perfect way to spend three days in Chicago? Whether it’s your first visit or your tenth, Chicago never disappoints with its skyline views, iconic eats, and vibrant neighborhoods. I put together the dreamiest 3-day Chicago itinerary packed with good food, unforgettable experiences, and some major “pinch me” moments.

Be sure to bookmark this 3-Day Chicago itinerary post so that you have it as a resource for your next trip. Let’s dive in!

Day 1: River Views and Rooftop Sips

Start your trip with an architecture tour on the Chicago River — trust me, this is a must! You’ll get a stunning, up-close look at the city’s famous skyline and learn all about the history behind the towering buildings. I always recommend the architecture tour but if it’s Summer time and you have a group, you absolutely HAVE to rent a boat for the day and go out on Lake Michigan to the Playpen. It’s the best view of the city and such a good time.

After working up an appetite, grab a classic Italian beef sandwich from @alsbeef or a Chicago-style hot dog from @portilloshotdogs. (Both are local staples — you honestly can’t go wrong!)

Next, head to @lhchicago for a rooftop drink. Sip something refreshing while soaking in breathtaking views of the city — it’s the perfect golden hour stop.

Wrap up your first day with a delicious dinner at either @rosemarychicago or @monteverdechi. Both spots serve up some seriously swoon-worthy plates, so be sure to book a reservation ahead of time!

Day 2: Cubs, Coffee, and Colorful Vibes

Start your morning with a coffee run at @sawadacoffee — the vibe here is seriously cool and the matcha latte is chef’s kiss.

Next, brunch it up at @trivolitavern. (If you’re into cozy tavern vibes mixed with a killer brunch menu, this is your spot.)

Now it’s time to head to iconic Wrigley Field for a Cubs game! There’s nothing quite like catching a day game here — the energy is contagious. Before or after the game, stroll around Wrigleyville and pop into The Cubby Bear for some live music and more Chicago fun.

If it’s not basbeball season, I highly recommend a Blackhawks hockey game or a Bear’s football game. And if none of those Chicago sports activities work out, there’s a good chance you might be able to catch a good concert in the iconic Chicago Wrigley Field or Soldier Field Stadium. We were able to see Morgan Wallen at Wrigley Field and George Straight at Soldier Field Stadium!

End the day with dinner at @happycamperchicago — the pizza, neon signs, and funky decor guarantee a good time.

Day 3: Scooters, Lakeside Views, and Deep Dish Dreams

For your final day, grab breakfast at the legendary @loumitchells565. It’s a Chicago institution, and their pancakes will change your life.

Rent a scooter or e-bike and cruise through downtown and around the lake. Take your time strolling along Michigan Avenue and the Chicago Riverwalk — there’s so much to see (and shop!).

Make a pit stop at the Starbucks Reserve Roastery for a flight of espresso martinis — because vacation rules, right?

Finally, cap off your trip with a deep dish pizza feast. You can’t go wrong with @loumalnatis or @pequodspizza. (Honestly, maybe try both and pick your fave.)

More Chic Chicago Restaurant Recommendations

Breakfast/Brunch

Foxtrot – A stylish café/market perfect for grabbing a coffee, breakfast sandwich, or some quick snacks before a busy day. They have a good lavender latte!

Pure Green – A go-to for fresh smoothies, juices, and healthy bowls if you’re looking to start your morning on a lighter note.

Beatrix – An airy spot offering a full breakfast menu with coffee, pastries, and healthy options.

Summer House – Dreamy California vibes meet cozy brunch favorites like pancakes, breakfast burritos, and fresh salads.

Lunch

Au Cheval – Home of the legendary cheeseburger — often called the best burger in America!

Ella’s BBQ – Finger-lickin’ good BBQ with a modern Chicago twist. Save room for the mac and cheese.

Texan Taco Bar – Casual spot for tacos that hit the spot after a busy morning exploring.

Ramen-San – Slurp-worthy ramen in a lively, casual setting perfect for lunch or a quick cozy meal.

Ema – Light, Mediterranean-style small plates in a sleek, airy setting.

Dinner

Monteverde – Handmade pasta heaven — a must-visit for any foodie.

Girl & The Goat – One of Chicago’s most famous spots, serving globally inspired small plates in a lively atmosphere.

Green Street Smoked Meats – Laid-back BBQ joint tucked away in the West Loop, serving epic brisket and craft beer.

Lyra – Chic Greek restaurant offering Mediterranean-inspired dishes and stunning decor.

The Dawson – Modern American dishes served in a beautiful rustic-chic space.

La Luna Chicago – Colorful Mexican plates, margaritas, and an ultra-fun atmosphere in Pilsen.

Lavaca – Newer hotspot specializing in Argentinian flavors and juicy steaks.

North Pond – Fine dining tucked inside Lincoln Park with beautiful pond and skyline views.

Hawksmoor – A British import delivering one of the best steakhouse experiences in Chicago. Vibey steakhouse for a business dinner or date night.

Tre Dita – Fresh Italian classics served in a stylish new space, perfect for an upscale date night.

Folklore – Cozy Argentine steakhouse with rich flavors and romantic vibes.

Cabra Chicago – Vibrant rooftop Peruvian restaurant by Top Chef’s Stephanie Izard.

Bonus: Chicago Icon Spots

RH Restaurant– Gorgeous restaurant atop RH Chicago, ideal for a boujee brunch or coffee date. They have one location near Old Town and another out in Oakbrook.

Ralph Lauren Restaurant – Upscale American food inside the RL flagship store, full of classic, chic vibes. They also have a coffee shop next door!

The Palm Court at The Drake – Traditional high tea in a luxurious setting at one of Chicago’s most historic hotels.

Where to Stay

The Hoxton – My #1 recommendation! Located in the heart of the West Loop, The Hoxton is effortlessly cool with chic rooms, rooftop dining, a speakeasy-style bar (Lazybird), and a lobby that’s always buzzing. Ideal for travelers who love style and convenience.

The Emily Hotel – A boutique gem in Fulton Market with modern, artsy rooms, a vibey rooftop bar, and a laid-back coffee shop. It’s perfect for creative travelers who appreciate design and love staying in a local-feeling neighborhood.

The Pendry Chicago – Housed in the iconic Carbide & Carbon Building on Michigan Ave, The Pendry brings modern luxury with art-deco charm. Think moody interiors, rooftop views, and a cocktail bar that feels straight out of a film noir.

21c Museum Hotel Chicago – A boutique hotel-meets-art-gallery just off the Magnificent Mile. Every hallway is an Instagram moment, and the rooms are sleek and artsy. Perfect for culture lovers and creatives.

The Langham Chicago – For a luxury five-star elegance, The Langham is unmatched. Nestled right on the river, it offers sweeping city views, a world-class spa, and timeless luxury just steps from the city’s best shopping and dining.

Chicago is the perfect mix of city adventure and laid-back lakeside vibes. From architecture cruises and rooftop cocktails to Cubs games and cheesy deep dish dreams, this 3-day itinerary has it all. Bookmark this for your next visit, and get ready to fall in love with the Windy City!

Keep up with all of my chic adventures in Chicago on my instagram where I share even more reccs and hot spots we’re trying.