3 days in Chicago: The Perfect Guide

ByPoints and Postcards
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Wondering how to make the most of 3 days in Chicago? You’re in the right place! As locals with insider knowledge of the city’s hidden gems and must-see attractions, we’re here to guide you through an unforgettable Chicago adventure. Whether it’s your first time exploring the Windy City or you’re a seasoned visitor looking for fresh experiences, we’ve crafted the perfect list of things to help you see, taste, and experience all that Chicago has to offer. Get ready for a trip full of iconic landmarks, unique neighborhoods, and local favorites.

How to get to Chicago

Chicago is an easy city to get to, regardless of your transport method.

Driving: If you’re driving, Interstate 94 (I-94) is one of the main highways that connects you to Chicago from the north, south, and west. It’s a key route from cities like Milwaukee, Detroit, and Indianapolis. Depending on where you’re coming from, I-94 will take you directly into the city. Be prepared for traffic, especially during peak hours, as Chicago is known for some of the worst traffic in the U.S. Once you’re in the city, there are plenty of parking options, but expect to pay for parking in most areas, especially downtown.

Flying into the city: Chicago is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW).

  • O’Hare International Airport (ORD) is the larger of the two and one of the busiest airports in the world. It’s located about 17 miles northwest of downtown Chicago, easily accessible via I-90 and the Blue Line of the Chicago Transit Authority (CTA), which offers a direct train ride into the city. O’Hare serves numerous domestic and international flights. O’Hare is a United Airlines hub and carries a fair amount of American Airlines flights, so this will likely be your airport if you’re flying.
  • Midway International Airport (MDW), located about 10 miles southwest of downtown, is smaller and typically handles more domestic flights. It’s a popular place to fly into for Southwest devotees. It’s easily accessible via I-55 and also has a CTA Orange Line station, providing a direct connection to downtown Chicago in about 25 minutes.

Traveling by Train: Amtrak services several routes to Chicago, including the Empire Builder, Lake Shore Limited, and Cardinal, which connect the city with other major regions across the U.S. If you’re traveling from nearby cities, the Metra commuter trains offer a convenient and affordable way to get into downtown Chicago from suburbs and surrounding areas. The main train stations are Union Station (for Amtrak and Metra services) and Ogilvie Transportation Center (for Metra).

No matter how you choose to get there, Chicago is well-connected and easy to access from just about anywhere.

When is the best time to visit Chicago?

There is something for everyone in Chicago – and possibly in every season. But depending on what you most want to do, some planning is required.Chicago is a city that thrives in every season, offering unique experiences no matter the time of year. Here’s a look at what to do in each season:

Spring

As the city shakes off the winter chill, spring brings Chicago’s outdoor spaces to life. Take a stroll through the blooming Chicago Botanic Garden or Millennium Park to enjoy the vibrant flowers. The Chicago Riverwalk is perfect for enjoying the warmer weather, and you can catch outdoor festivals like Chicago’s Blues Festival and the Chicago Cubs’ home opener at Wrigley Field. It’s also a great time for cycling along Lakefront Trail as the city’s parks begin to bloom. Bring a jacket though – spring in Chicago, particularly early spring, might remind you of winter in some locations.

Summer

Chicago’s summer is legendary, with endless outdoor events and activities. We jokingly tell people that we live in Chicago just for the summers. Head to the lakefront for beaches, picnics, and boating on Lake Michigan. Summer also brings an exciting festival season, including Lollapalooza, Chicago Air and Water Show, and Grant Park Music Festival. Explore Millennium Park for free concerts and outdoor movie nights. Don’t miss the lively Navy Pier, which offers rides, games, and dining with stunning views of the city skyline.

Fall

As the leaves change, fall in Chicago is a stunning time to explore the city’s parks and neighborhoods. Enjoy a walk through Lincoln Park and Grant Park to see the fall foliage. The crisp air makes it perfect for cozying up at a café or checking out fall-inspired markets like Harvest Days or Pumpkin Fest. Football season kicks off, with the Chicago Bears at Soldier Field, while Chicago’s architecture and food scene take center stage with Open House Chicago and Chicago Gourmet Festival.

Winter

While winter can be cold, Chicago embraces the season (is there really a choice?). Ice skate at the iconic Ice Rink in Millennium Park or head to Navy Pier for the Winter WonderFest. Explore the city’s holiday markets, like the Christkindlmarket, and warm up with delicious winter treats like hot chocolate from local cafés. The city also transforms into a winter wonderland, with festive lights and cozy events.

No matter the season, Chicago’s energy and diverse offerings make it an exciting city to visit year-round!

Where to stay in Chicago

Chicago is a city of neighborhoods—officially divided into 77 community areas and over 200 recognized neighborhoods, each with its own identity. If it’s your first visit, the most convenient place to stay is downtown, near the Loop, River North, or Streeterville. You’ll be steps from landmarks like Millennium Park, Navy Pier, the Chicago Riverwalk, the Art Institute, and endless shopping and dining.

Here’s a mix of centrally located hotels, ranging from historic icons to sleek modern stays:

Best Hotels for First-Time Visitors

  • Hyatt Regency Chicago
    The world’s largest Hyatt, with over 2,000 rooms. Right on the Chicago River and connected to the Pedway system—great for exploring the Loop and Riverwalk without going outside in winter.
  • Park Hyatt Chicago
    Sophisticated luxury steps from Michigan Avenue, with beautiful lake views, an excellent spa, and refined service.
  • Chicago Athletic Association Hotel
    Historic 19th-century building turned trendy hotel across from Millennium Park. Great public spaces, plus Cindy’s rooftop bar for amazing views.
  • The Drake Hotel
    Classic Chicago elegance at the north end of the Magnificent Mile. Perfect if you love historic hotels and Lake Michigan views.
  • The Westin Chicago River North
    Modern rooms overlooking the river, with a great location for both business and leisure travelers. Walkable to the Loop, River North dining, and theaters.
  • Fairmont Chicago, Millennium Park
    Spacious, modern rooms near Millennium Park and Maggie Daley Park. Quiet but central.
  • Loews Chicago Hotel
    In Streeterville, steps from Navy Pier and Michigan Avenue.
  • JW Marriott Chicago
    Classic luxury in a historic Daniel Burnham-designed building. Spacious rooms and a beautiful lobby in the Financial District.
  • Kimpton Gray Hotel
    Stylish property in a historic skyscraper.

Getting around Chicago

Depending on where you stay, Chicago’s public transit system (the CTA) might be your best bet at getting around the city. That way, you don’t have to combat traffic or worry about finding and paying for parking. You can purchase a 1-Day, 3-day, or 7-day pass for the CTA and have unlimited rides on all CTA buses or trains.

The L or “el” (elevated) train lines in Chicago will get you to a lot of the neighborhoods, but you may have to switch between certain lines – for example. The red line can take you north-south, but if you want to go from say Lakeview to Wicker Park on the L, you’ll need to take the red line into the loop and then get on the blue line to go out to Wicker Park.

Buses may be an option but also could leave you stranded in traffic. Download Google Maps if you plan to use public transit as it will clearly lay out the best route to take.

Want to drive? Plan on venturing to a variety of neighborhoods? If renting a car is in the cards for you, check out SpotHero and book your parking ahead of time, especially if you’re going to the Loop. If you’re venturing into neighborhoods like Lincoln Park, you’ll likely be able to find street parking without relying on SpotHero. Just be on the lookout for residential permit parking only – you don’t want to go home with a parking ticket as your souvenir.

The Best Things to Do in Chicago

Take a River Cruise

The number one thing I recommend to all first-time visitors to Chicago is doing a Chicago Architecture Cruise. It’s an unforgettable way to explore the city from the iconic Chicago River while gaining fascinating insights into the history and evolution of Chicago through its stunning architecture. This is such a fun thing to do that we (as residents of Chicago) have done it several times.

Visit The Bean

The Bean, also known as Cloud Gate, one of Chicago’s most well-known landmarks and is a popular spot for tourists. Take some selfies to share with your friends of you in this iconic art installation. Keep walking through Millennium Park for art, gardens, and attractions to explore and enjoy.

Go to the museums

Chicago is home to world-class museums, including the Art Institute of Chicago, the Field Museum, the Museum of Science and Industry, the Shedd Aquarium, and the Adler Planetarium. Museum Campus is home to the Field, the Shedd, and the Adler for easy access to a jam-packed day full of museum visits (if that’s your thing).

The Art Institute of Chicago is one of the world’s great art museums, renowned for its impressive collection of Impressionist works, modern masterpieces, and iconic pieces like A Sunday on La Grande Jatte. If you’re looking for interactive fun, the Museum of Science and Industry offers hands-on exhibits and is a holiday favorite for its Christmas Around the World and Holidays of Light. Curious about dinosaurs? Visit the Field Museum to see Sue, the largest and most complete Tyrannosaurus rex specimen ever discovered. The Adler Planetarium, the first planetarium in America, offers fascinating insights into astronomy and space. And if ocean life fascinates you, the Shedd Aquarium is home to more than 20,000 aquatic animals waiting to be explored.

Want a museum that’s a bit less visited? Check of the Museum of Contemporary Art, the International Museum of Surgical Science, and Chicago History Museum for fewer crowds but tons of interesting exhibits. Looking to visit a few of these? Check out the Chicago City Pass for access to lots of attractions.

Walk out on the Sky Deck

Want incredible views of Chicago? I hope you’re not afraid of heights. See the city from a glass box in the sky at the Willis Tower Sky Deck. The Skydeck at Willis Tower (formerly known as the Sears Tower) offers one of the most thrilling experiences in Chicago. Located on the 103rd floor, the Skydeck provides stunning 360-degree views of the city, Lake Michigan, and beyond. For an extra adrenaline rush, step out onto The Ledge—glass-floored balconies that extend out from the building, allowing you to look straight down to the street below.

See a show at Second City

A visit to Second City in Chicago is a must for visitors to Chicago! As one of the most iconic improv and sketch comedy theaters in the world, Second City has launched the careers of countless famous performers, including Tina Fey, Steve Carrell, Stephen Colbert, Bill Murray, Amy Poehler, and Jordan Peele. Whether you’re attending a show with a rotating cast of talented comedians or enjoying one of the hilarious, topical performances, you’re guaranteed a night full of laughs.

Spend time at the Zoo

A visit to Lincoln Park Zoo offers a fun experience for visitors of all ages. Located in the heart of Lincoln Park on the North Side of Chicago, this free, family-friendly zoo is home to a wide variety of animals from around the world, including lions, gorillas, and penguins. Explore beautifully landscaped grounds, enjoy seasonal exhibits, and even visit the Farm-in-the-Zoo for a taste of rural life in the city. If you’re in Chicago from mid-November through early January, purchase tickets to Zoo Lights at the Lincoln Park Zoo.

Shop on Michigan Avenue

Take some time to walk along Michigan Avenue, also known as the Magnificent Mile. This iconic stretch of street offers an unparalleled shopping experience, with everything from luxury boutiques and high-end department stores to trendy shops and unique local retailers. Whether you’re looking for designer fashion at stores like Nordstrom and Gucci, or searching for one-of-a-kind finds in charming specialty shops, Michigan Avenue has something for everyone.

Take in a sporting event

Chicago is a sports city. And while many of the Chicago teams are currently in down years (or decades), it’s still fun to root for the home team. Depending on the time of year you’re visiting Chicago, buy tickets for the Bears, Blackhawks Bulls, Cubs, Red Stars, Sky, or White Sox. College more your speed? DePaul University, Loyola University, and University of Chicago are all in the city with Northwestern University just north in Evanston.

Check out a local event

There is no shortage of events, street fairs, festivals, etc. in Chicago throughout the year. It’s one of my favorite things about Chicago because you can always find something going on. And depending on your interest, you’ll probably find at least one that intrigues you. Here are few to think about:

Venture out into the neighborhoods

Remember those 77 community areas and 200 neighborhoods? If you only stay “downtown”, you’ll miss a lot of what makes Chicago such an amazing place. This one deserves a special section because there truly is something for everyone. Here are just a few neighborhoods to add to your list.

Andersonville

In 2021, Andersonville was voted one of the coolest neighborhood’s in the entire world. Yep, not just the U.S. – in the world. Andersonville was originally home to Swedish immigrants, and its Swedish roots are still evident today as you stroll up and down Clark Street. Take a visit to the Swedish-American Museum, stop into charming stores like Four Sided, or eat at one of many delicious places. Some of our favorties in Andersonville: Little Bad Wolf, Lost Larson, HopLeaf, and Middle Eastern Bakery.

Chinatown

A visit to Chinatown in Chicago offers a vibrant mix of culture, cuisine, and history. Start by exploring Ping Tom Memorial Park, a serene riverside spot with beautiful walking paths, traditional Chinese architecture, and stunning views of the city skyline. For food lovers, QXY Dumplings is a must-visit, serving up delicious, hand-crafted dumplings and other authentic Chinese dishes that will leave your taste buds craving more. Beyond the food, Chinatown is full of unique shops, bustling markets, and cultural landmarks like the Chinese-American Museum of Chicago and the iconic Dragon Gate.

Fulton Market

Fulton Market is one of Chicago’s most rapidly evolving neighborhoods. Once a meatpacking district, it has transformed into a trendy hotspot filled with upscale restaurants, craft breweries, art galleries, and unique boutiques. The area is known for its vibrant food scene, offering everything from gourmet coffee at local cafes to world-class dining at spots like The Aviary and Girl & The Goat. Whether you’re exploring the innovative Fulton Market Kitchen, enjoying the lively atmosphere of the Fulton Market Collective, or checking out the murals and street art that adorn the district, there’s always something new to discover.

Hyde Park

Home to the prestigious University of Chicago, Hyde Park offers a mix of history, culture, and natural beauty. Visit the Museum of Science and Industry, take a walk through the Japanese Garden, or check out the beautiful campus of the University of Chicago. Hyde Park is also where the Obamas once lived, and you can visit their former home in this charming, intellectual neighborhood. For a taste of local cuisine, head to Roux, a cozy neighborhood gem offering Southern-inspired dishes with a modern twist.

Lincoln Park

A family-friendly neighborhood with a mix of nature, culture, and shopping, Lincoln Park is home to the Lincoln Park Zoo (one of the oldest free zoos in the U.S.), the beautiful Lincoln Park Conservatory, the Peggy Notebart Museum, and lush green spaces. The area also offers a wide variety of restaurants and boutiques, especially around Armitage Avenue.

Wicker Park

Wicker Park is an eclectic neighborhood with a laid-back, creative atmosphere. The area is filled with cool coffee shops, stylish bars, and locally-owned shops. You’ll also find The 606, an elevated park and trail system perfect for biking or walking.

Where to eat in Chicago

Chicago has a tremendous food scene. From Michelin-star restaurants and Bib Gormand spots to local gems, you truly can find every type of food in Chicago. Here are just some of our favorites:

  • Little Bad Wolf – bar food with a twist in Andersonville, they serve burgers, bao buns, and tacos (among other things). My personal favorite is the elote topped with beer-battered avocado.
  • Cafe Ba-Ba-Reeba – Spanish tapas in Lincoln Park. The brussels sprouts salad with manchego cheese is a must, as is the paella of your choice.
  • Aba – spending some time in trendy Fulton Market? This is the place we keep going back to. A Mediterranean restaurant with a California influences serving food to satisfy any diners. Always part of our order? The truffle baked orzo, short rib hummus, crispy potatoes, and brussels sprouts.
  • Alla Vita – don’t miss the vodka rigatoni, the perfectly crispy wood-fired bread, and the deliciously charred broccolini—all must-try dishes.
  • Bavette’s Bar & Boeuf – Bavette’s Bar & Boeuf offers a cozy, speakeasy-style atmosphere and exceptional steakhouse fare, with their tender dry-aged steaks and signature cocktails making it a top choice for a special night out.
  • Au Cheval – Au Cheval is a must-visit in Chicago for burger lovers, renowned for its indulgent, mouthwatering cheeseburger, often hailed as one of the best in the city. They have a few Small Cheval locations around the city if you can’t get into Au Cheval.

If you want to get deep dish pizza in Chicago, we suggest Lou Malnati’s or Pequod’s. Lou Malnati’s is a classic choice, known for its buttery, flaky crust and rich tomato sauce. If you’re looking for something a little different, Pequod’s serves up a caramelized, crispy crust that’s a local favorite. For Chicagoans, tavern style pizza is more of a regular get than deep dish.

Where to get coffee in Chicago

Chicago is home to so many unique coffee shops that you should try as many as possible during your visit. Some of our favorite places to consider:

  • Metric Coffee – Located just west of Fulton Market, Metric is a small-batch roastery known for its meticulously sourced beans and smooth, expertly crafted brews that make it a favorite among coffee aficionados.
  • Side Practice Coffee – A hidden gem on Foster, perfect for anyone heading to the North Side. They have a seasonal Thin Mint latte that’s a must-order and P2 is partial to their ube oatmeal cream pies.
  • Intelligentsia Coffee – A Chicago institution, Intelligentsia is known for its direct-trade beans and dedication to artisanal brewing.
  • Heritage Bikes & Coffee – This café seamlessly combines bikes and brews, offering a great spot to sip on your coffee while browsing through their selection of vintage bicycles.
  • Wormhole Coffee – A fun, retro-inspired café in Logan Square with a playful vibe. Famous for its delicious coffee and Instagram-worthy décor, including an old-school arcade game.
  • Backlot Coffee – With two locations (Irving Park and Lincoln Square), Backlot has earned a loyal following for its friendly service and delicious offerings, including their signature oatmeal cookie latte—a sweet treat for coffee lovers.
  • Coffee and Tea Exchange – A local favorite for both beans and loose-leaf teas, this charming shop also makes monthly themed menus (think Taylor Swift or Rocky Horror Picture Show).
  • Sawada Coffee – If you’re looking for something a little more adventurous, Sawada offers fancy matcha lattes and Japanese-inspired coffee creations.

Final Thoughts: 3 days in Chicago

This wraps up our guide on how to spend 3 days in Chicago. There truly is something for everyone in the wonderful city that we call home.

If you have a shorter weekend, hit the top spots. With some more time, you can explore the amazing neighborhoods across the city.

Looking for more Midwest content? Consider taking a drive east on 94 and visiting Ann Arbor!