Chicago Itinerary: Plan The Perfect 3 Day Trip

Are you planning a Chicago trip and wondering how to make the most of your time in the city? Look no further! With so much to see and do in the Windy City, it can be overwhelming to plan an itinerary. We have created a detailed 3-day Chicago Itinerary that will help you experience the best of what this city has to offer. From iconic landmarks to delicious food and vibrant neighborhoods, this itinerary will ensure you maximize your Chicago trip. So grab your walking shoes and get ready to explore the diverse and exciting city of Chicago.

Chicago Trip Planner Itinerary

Day 1 -Morning

  • Breakfast at the Goddess & The Baker
  • Chicago River Walk or Chicago River Cruise
  • Lunch at Revival Food Hall 

Day 1- Afternoon 

  • Museum Option   or Wrigley Field Tour or Game
  • Enjoy Millenium Park 

Day 1- Evening

  • Dinner at Acanto restaurant 
  • Enjoy a Chicago Theater

Day 2- Morning 

  • Breakfast at Starbucks Reserve - The Roastery Chicago
  • Shop on the Magnificent Mile 
  • Visit the Chicago Water Tower 

Day 2- Afternoon

  • Lunch at Sayat Nova
  • Explore the Museum of Contemporary Art 
  • Afternoon views and sunset at 360 CHICAGO Observation Deck 

Day 2 - Evening

  • TILT - thrill ride
  • CloudBar for drinks
  • Dinner at Nomi Kitchen or Navy Pier
  • Fun at Navy Pier 

Day 3 -Morning

  • Breakfast at Wheat's End Cafe and Bakery
  • Lincoln Park Zoo Visit and Lincoln Park Boardwalk
  • Alternate indoor options: Peggy Notebaert Nature Museum or Chicago History Museum 

Day 3 -Afternoon 

  • Lunch at Patio Brauer or Nookie's on Wells
  • Walking tour of the Old Town Triangle 
  • Optional visit to Shedd Aquarium

Day 3 -Evening 

  • Evening - Drinks at the Old Town Ale House 
  • Dinner at Topo Gigio 
  • Catch a comedy show at Second City or Zanies 

 Chicago Trip Planning Tips

  • When to visit Chicago
  • Getting around Chicago
  • Save Money on Attractions with a Chicago City Pass or Go City®
  • What to Pack for a Trip to Chicago
  • Tips for Staying in Chicago


Kickstart your Chicago journey in and around the Chicago Loop Neighborhood. This area is the heart of downtown Chicago and the central business district. One may think it's quiet after 5 pm and a ghost town on weekends, but its events, theaters, and parks make it an exciting destination any time of the year.

Start with a hearty breakfast at the Goddess and the Baker, located at the intersection of Wacker & LaSalle. This café is renowned for its extensive coffee selection and creative brunch menu featuring classic and innovative dishes. Fuel up for the day with one of their artisanal sandwiches or decadent pastries. 

After breakfast, take a stroll along the Chicago River Walk. 

The river walk is a 1.25-mile-long path along the Chicago River to see the city's infamous architecture and attractions and get a first-hand perspective of areas you may want to see again during your visit. There is much to see along the pathway; it is continuous from Lake Street to the lakefront, or you can take the vertical stretch from Upper Wacker Drive to the waterway. 

Another way to see Chicago's outstanding architecture and the main sites is on a Chicago River Cruise. Join a tour with exciting narration and details of the legendary people who designed and built Chicago. Even if the weather isn't cooperating, this cruise allows you to sit indoors or outdoors. Relax and enjoy the 90-minute tour for an exciting sightseeing tour in the city.

Views from Above Chicago



When hunger strikes, head to Revival Food Hall for lunch. This all-local dining concept spotlights the best of Chicago’s culinary scene under one roof. Whether you're craving ramen, tacos, or something vegan, you'll find something to satisfy your taste buds here.

Museum of your Choice 

As the afternoon rolls in, choose an indoor activity from three of the best museums in the United States, such as the Art Institute of Chicago, one of the oldest and largest art museums in the United States and home to over 300,000 works of art. You'll find pieces from every era, from ancient times to the contemporary period. Alternatively, visit the Field Museum, which boasts the status of one of the world's leading natural history museums. Its exhibits are immersive and span from ancient cultures to modern-day scientific discoveries, with a staggering collection of over 24 million objects, contributing to the museum's status as a global destination for educational and informative experiences.

If museums aren't your thing and you would rather be outside and enjoy some sports, head to a baseball game or take a tour of Wrigley Field, one of Chicago’s gems with over 100 years of history! You can watch a game, wander through the seats and concessions, or tour the stadium. Every Cub fan—big or small—will love stepping onto the field where so many greats have played, sitting in the dugouts, and more!

Wander Millennium Park

If you are craving a little more outdoor time after your museum visit, wander around Millennium Park and check out the Lurie Gardens and the Crown Fountain, and if you are lucky, there may be a free concert at the Jay Pritzker Pavilion. When you visit Chicago, you may see The Bean, officially known as Cloud Gate, the stainless steel sculpture that reflects the city's skyline and the clouds above and has become an iconic symbol of Chicago. The Bean is closed for renovations until Spring 2024, but we have some exciting options for you to enjoy in and around the park if the upgrades are still in progress.

Visit Chicago for 3 days and get to a game at Wrigley Field!


As evening falls, indulge in an unforgettable dining experience at Acanto restaurant, an award-winning Italian restaurant near Millennium Park. With a menu that beautifully balances traditional and contemporary Italian cuisine, it's the perfect setting for a sophisticated yet relaxed dinner. 

Round off your day with a show at one of Chicago's World-Famous Theaters. 

Take advantage of the thriving theater scene; the most famous is the iconic Chicago Theater in downtown Loop.  Alternatively, choose a theater slightly off the beaten path. The Chicago Magic Lounge, in the Andersonville neighborhood, offers a unique blend of a speakeasy, magic show, and theatrical production that you won't find anywhere else. Enter through the secret door to a laundromat and be transported into a mysterious location. Find a list of the top Chicago theaters here.

With two more days to go, rest well, knowing you have plenty more exciting adventures to look forward to!

Chicago Theater District - a Must do activity on a 3 day Chicago Itinerary.


Rise and shine for your second day in Chicago and gear up for another round of adventures. Begin your day with a special cup of coffee and breakfast at Starbucks Reserve - The Chicago Roastery, the largest Starbucks in the world, located on the Magnificient Mile. With four stories and more than 35,000 square feet of space, the cafe is a must-visit for coffee lovers and is known for its immersive coffee experience and impressive selection of unique drinks, pastries, and food selections. 

Once you've sufficiently caffeinated, it's time to indulge in a shopping spree on the Magnificent Mile. This bustling district offers a blend of high-end stores, trendy fashion outlets, and major department stores, making it a shopper's paradise. While window shopping around the area, visit the iconic Water Tower, one of the few structures that survived the Great Chicago Fire of 1871 and an important symbol of the city's resilience.

As the clock strikes lunch hour, take a ten-minute walk to refuel at Sayat Nova, an award-winning Armenian restaurant serving authentic and flavorful dishes since 1970. Their diverse menu includes meat and vegetarian options to tantalize your taste buds.

Chicago Water Tower


After lunch, soak in some culture at the nearby Museum of Contemporary Art, which houses a vast collection of artwork dating from 1945 to the present. Take your time to admire the thought-provoking exhibits and installations, and engage in a dialogue with the art.

In the late afternoon, make your way to 360 CHICAGO, the Observation Deck on the 94th floor of the former John Hancock Center. Witness one of the best places in the city for sunset when the breathtaking 360 panoramic view of the cityscape transforms under the golden hues.  For an extra jolt of adrenaline, add a ride on TILT to your ticket— one of the highest thrill rides in the world, for a unique and thrilling view of the city. Participants can lean outwards on a glass window that tilts forward to a 30-degree angle, offering an exciting perspective of the Windy City.

360 CHICAGO Observation Deck


With your 360 CHICAGO entrance ticket, stay as long as you like. As the night descends, raise a toast to your second day in Chicago at CloudBar, a stylish lounge offering exquisite cocktails, snacks, and more views of Chicago's brilliant skyline. 

Post-drinks, treat yourself to a sumptuous dinner at either Nomi Kitchen, known for its upscale American fare and stunning views, or opt for a more casual dining experience at Navy Pier, which offers a diverse range of food options from pizza to seafood.

End your day on a fun note by enjoying the various games at Navy Pier; there are always fun things to do at the Pier, like free concerts, cultural attractions and games and rides like the iconic Ferris wheel. Wrap up the day with a sweet treat (like ice cream) with the backdrop of the summer fireworks lighting up the sky. 

Remember, your trip to Chicago is more than halfway over - the city still has plenty more to offer, so save some energy for what's coming next!

TILT at 360 CHICAGO Observation Deck


Get ready to embrace the final day of your Chicago trip with the same enthusiasm you started with. Start your day right with breakfast at Wheat's End Cafe and Bakery; located near the Lincoln Park Zoo, this bakery cafe offers a mouth-watering selection of breakfast dishes and artisanal baked goods that are sure to fuel you up for the day's adventure.

After breakfast, spend your morning at the Lincoln Park Zoo. This all-ages attraction is home to more than 200 species of animals and home to one of the last free admission zoos in the country. Built in 1868, it’s also one of the oldest. Beyond the amazing exhibits, the summer months are filled with special events like picnics, block parties, and wine tastings.

After your zoo visit, take a leisurely stroll along the Lincoln Park nature boardwalk and enjoy stunning views of the Chicago skyline. Along the boardwalk, make a stop at The Honeycomb—a gorgeous piece of contemporary art that makes an interesting shot in all kinds of lighting, both day and night. If the weather is not cooperating, don't worry! There are plenty of indoor options. The Peggy Notebaert Nature Museum and the Chicago History Museum  are both fantastic nearby alternatives offering interesting facts, knowledge and interactive exhibits.



Before you leave the Lincoln Park area, grab lunch at the Patio at Café Brauer right off the Nature Park Boardwalk or head to Nookies on Wells, a 50-year-old establishment serving up American and Classic Diner comforts.

Visit the Old Town Neighborhood

In the afternoon, immerse yourself in the history and charm of the Old Town Triangle neighborhood to the north on Division Street on the south side and on Wells and Clark Streets. This historic area is best known for its well-preserved Victorian homes, tree-lined streets, quaint shops and quality restaurants. Consider taking a walking tour to appreciate the area's rich history and unique character fully.  If the weather doesn't cooperate, consider visiting the Shedd Aquarium. This exciting indoor public aquarium, with a diverse collection of over 32,000 marine animals and creatures worldwide, offers a rare and fascinating opportunity to discover marine life and its preservation.


Unwind at the Old Town Ale House

As evening approaches, take a load off your weary feet and unwind with a drink at the Old Town Ale House. Known as the "Best Dive Bar in Chicago," this watering hole has been serving patrons since 1958 and offers an impressive selection of beers. It's colorful history and quirky art collection make it an ideal place to relax and soak in the local culture.


For your final dinner in Chicago, Bring your appetite to one of the best Italian restaurants in Chicago and an Old Town staple—Topo Gigio. Book ahead in the cozy dining room, or find a spot in the garden during the summer months. It's the perfect place to reminisce about your Chicago adventure over a delicious meal. 

Catch a Comedy Show

No Chicago itinerary would be complete without experiencing its legendary comedy scene. The greatest comedians in America got their start with improv and sketch comedy in Chicago.  So, wrap up your night and three-day Chicago journey with laughter at two of Chicago's Comedy Clubs in the area. The first option is Zanies Comedy Club—a staple of Chicago's comedy scene since 1978. The club hosts local and national acts and has seen the likes of Joan Rivers, Jerry Seinfeld, and Ellen DeGeneres grace its stage. Alternatively, check out Second City, the club that is a training ground for some of the biggest names in comedy. From John Belushi to Tina Fey and Steve Carell, Second City alumni have made their mark on the world of comedy. The club's mainstage shows are a must-see.

And just like that, your 3-day whirlwind tour of Chicago comes to an end. But remember, this is just a taste of what The Windy City has to offer. Whether it's the food, the history, the architecture, or the vibrant nightlife, there's always more to explore in Chicago!

Chicago Trip Planning Tips

When to Visit Chicago
Deciding on what time of year to visit Chicago largely depends on what you want to experience. 
Winter: The city turns into a magical winter wonderland from December to February; though quite cold, there's holiday charm with Christmas markets and ice skating.
Spring (March-May) tends to be rainy, but the city’s parks are stunningly verdant.
Summer (June - August) is vibrant and filled with numerous events, including popular summer festivals such as the Lollapalooza Music Festival, Taste of Chicago Food Festival, and city-wide beach openings. 
Autumn (September - November) is great for its fall foliage and the comfortable weather. 

Getting Around Chicago 

Getting around the city of Chicago is quite convenient due to its extensive and well-run public transportation system. 

The 'L' train (short for 'Elevated') operates across eight lines, servicing all parts of the city and even reaching into neighboring suburbs. Buses run throughout the city as well. Alternatively, there are many options for bike rentals, which are quite popular for leisurely rides along Lake Michigan or through the many city parks. Of course, traditional taxis and Uber are widely available. Find all the popular maps, including transit, bike paths, attractions and more, to help you get around Chicago.

Save Money on Attractions with a Chicago City Pass or Go City®

To save time and money on attractions in Chicago, a Chicago Attractions Pass is the perfect way to visit the renowned sights and, plan activities and make your Chicago Itinerary dollars go farther. Find out Chicago Pass options, covering what each includes, the prices, and more. Which Chicago Pass is right for you? Find out before you go. 

What to Pack for a Trip to Chicago

When it comes to packing, keep in mind Chicago’s weather during your visit. This city is known for its unpredictable weather changes; hence, it is always safe to pack layers regardless of the season. Summers can be quite warm, so light clothing is advised, but carry a light jacket or cardigan for sudden temperature drops. Winters are very cold, so pack your heavy coat, gloves, and a hat. Always include comfortable shoes, as Chicago is a walking city with many amazing architecture and scenery to enjoy.

Tips for Staying in Chicago

There's a plethora of options when it comes to where to stay in Chicago. If it's your first visit, downtown is a recommended area to base yourself. You'll be in the heart of the city and within walking distance of major attractions like The Art Institute, Navy Pier, and the Magnificent Mile. The Loop, which is part of the downtown area, is known for its stunning architecture. Other vibrant neighborhoods to consider include Lincoln Park, which boasts green spaces and a zoo, or the artistic, hipster-friendly neighborhood of Wicker Park. Chicago has accommodations that suit every taste and budget, ranging from luxurious hotels to cozy guest houses.

For more Chicago Itineraries and tips, visit our blog about things to do in Chicago any time of year.

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