The Perfect Chicago Weekend Itinerary

By the Backseat View

Chicago is one of those cities that surprises you.

You expect skyscrapers and busy streets, but what you find is a stunningly beautiful city filled with unforgettable views, art and legendary food. I knew Chicago was built to be more beautiful than New York’s buildings and Pittsburgh’s bridges, but I didn’t really believe it. Consider me proved wrong.

Whether you’re planning a couples’ getaway, a family adventure, or a girls’ weekend, Chicago delivers a lot in just a few days.

From iconic deep-dish pizza to breathtaking skyline views, river cruises, and baseball, this Chicago weekend itinerary packs in the city’s biggest highlights without feeling rushed.

Chicago Travel Guide

Chicago somehow feels both energetic and relaxed due to the calming river. Whether it’s your first visit or your fifth, three days gives you enough time to experience the architecture, savor the food, enjoy the lakefront, and explore some of the city’s most famous neighborhoods. While the Chicago Weekend Itinerary plans for three days, I’ll give you enough options to build a week-long itinerary.

I’ll let you in on a secret: Chicago is NOT Windy.

The Windy City is basically a nickname for the politicians who fought so hard to get Chicago on the map. It’s like the 20^th windiest city in America. For real wind-gust experiences, that’s a Midwest trip.

Come along as we spend the perfect weekend in Chicago exploring iconic attractions, delicious food, and unforgettable skyline views.

It’s hopeless for the occasional visitor to try to keep up with Chicago- she outgrows his prophecies faster than he can make them. – Mark Twain

Before we take off, here are a few Chicago Travel Tips.

Chicago Travel Tips

• Wear comfortable walking shoes. You’ll easily log several miles today.
• Uber is the easiest option and costs around $16 a trip, which is great for a family.
• Chicago’s train system is affordable, above ground, and feels safe.
• We experienced zero sketchiness with transportation, walking, or the city itself.
• You can take the L Train from the airport since it’s faster and cheaper than rideshares.
• The Chicago Pedway is an underground pedestrian walkway system to beat the weather.
• Buy attraction tickets and make restaurant reservations in advance.
• Bring a jacket for nighttime events.
• The City Pass can save money along with riding the Big Red Hop-On-Hop-Off Bus.
  

Chicago Weekend Itinerary

Day 1: Magnificent Mile Shopping, Pizza & Sunset Views

Afternoon: Arrive & Explore the Magnificent Mile

• After checking into your hotel, head to the Magnificent Mile. This famous 13 block stretch of Michigan Avenue is filled with 460 stores, 275 restaurants, 60 hotels and iconic Chicago architecture.
• Calling all Muggles! Don’t miss the Harry Potter Shop. Grab a frozen Butterbeer while browsing exclusive merchandise.
• Eat Garrett Popcorn. It’s famous with a mix of caramel and cheddar.
• The Water Tower Place is a 74-story skyscraper with an 8-level atrium mall with over 100 stores, a variety of restaurants, and a Broadway Playhouse.
• Come grab a bite at The Hello Kitty Cafe, which offers counter service for character treats and a 90-minute afternoon tea party on the second floor in the pink Bow Room.
• This is NOT New York’s Times Square, so all these shops close by 7 or 9 pm.

5:00 PM – Dinner at Gino’s East

No trip to Chicago is complete without authentic deep-dish pizza. Since you are shopping near this legendary establishment, grab a place in line.

Plan to arrive at Gino’s East around 5:00 PM to beat the peak dinner rush. Even then, expect approximately:

• 30–45-minute wait for a table
• Around an hour for your meal
• Deep-dish pizza takes 45 minutes to bake, but it’s worth planning around.
• If you finish before seven, then visit a few more shops.

7 PM – 9 PM 360 CHICAGO Deck

• After dinner, walk one block to 360 CHICAGO for incredible panoramic views over the city and Lake Michigan.
• Try to reserve your 7 PM tickets a month in advance, around sunset, for the best photos. You get daylight views, sunset over the city, then nighttime with all the lights, so it’s magical.
• There’s a bar with drinks and snacks for the two-hour sunset party. The tickets cost around $50 each.

Is TILT Chicago Worth It?

The optional TILT attraction leans visitors outward over Michigan Avenue. Personally, I didn’t think the additional cost was worth it.

Chicago View Options

• Sky Deck Chicago is an observation deck on the 103rd floor of the Willis Tower.
• LondonHouse Rooftop offers incredible views without the price of an observation deck. It’s a historic luxury hotel with a perfect location along the Chicago River and a tri-level rooftop bar. Make a reservation for LH22 Rooftop.
• North Avenue Beach with the skyline in the background
• Cindy’s Rooftop is a popular upscale restaurant on the 13th floor of the Chicago Athletic Association, known for stunning views of Millennium Park and Lake Michigan. You need reservations.
  

Day 2: River Cruise, Riverwalk & Chicago Classics

9 AM: Breakfast near the Riverwalk

• Wildberry Pancakes Café for unique pancakes
• River Roast- river views
• Tiny Tapp Café – river views
• Yolk- river views
• Goddess and the Baker for breakfast sandwiches with an artistic vibe.
  

11 AM: Chicago Architecture River Cruise

• An 11 am tour means arriving at 10:30 and catching an Uber or walking this way around 10 am.
• Give yourself time to get lost, since we did. Our Uber driver insisted on dropping us off at the Navy Pier, since all boat tours leave from there. However, Wendell departs from the Riverwalk in town, as my address stated.
• Parking in downtown is $40 and up, so it’s easier to Uber.
• Tours come in all sizes, but the 45-minute tour was perfect for my teenagers, who loved it, by the way. Adult parties, go for the 90-minute tours, since the views are worth it.

Are you ready to start your day with the Best Thing to DO in Chicago?

Wendella Tours

We chose the Wendella 45-minute tour, and it ended up being one of the highlights of the entire trip. Even if you’re not an architecture enthusiast, the guides make Chicago’s history fascinating. The buildings reflect one another and your boat. While birds live on the buildings designed to host them. I was so impressed with the beauty of the buildings. This tour was everyone’s favorite Chicago activity.

Reserve tickets weeks in advance, especially from late spring through fall.

TIP: The Chicago Water Taxi is $10, a cheap way to enjoy the city from the river.

Lunch Along the Riverwalk

After the cruise, stay on the Riverwalk for lunch. You’ll want to stay forever since it’s so peaceful. Choose a patio table if the weather cooperates—you’ll have relaxing views of the river while watching tour boats pass by. Meals on the Riverwalk just sink into your core memories, filled with peace, friends, and a beautiful environment. I’ll be forever grateful to have experienced it.

Great lunch options include:

• O’Brien’s Riverwalk Café
• Beat Kitchen on the Riverwalk
• Tiny Tapp & Café

After lunch, walk the length of the Riverwalk, stopping for photos, public art, and people watching.

The Riverwalk at night is a completely different atmosphere and just as magical.

River Crossing

The best streets to cross the Chicago River are Michigan Avenue, State Street, and Wells Street. You will ask yourself, “How do we cross?” So, go ahead and memorize Michigan, State, and Wells.

If you can find the power to walk away from the Riverwalk, there’s more to explore.

Afternoon: Theatre District & Millennium Park

Spend the afternoon exploring several of Chicago’s iconic landmarks.

Theatre District

Walk a few streets over toward the historic Theatre District. There’s always a Broadway tour, so consider seeing an evening performance. With over 250 theaters across the city, there’s a show for everyone.

Millennium Park

No first visit is complete without seeing the Cloud Gate (“The Bean”) and strolling through Millennium Park. This is also where the famous photo stop is with the buildings behind you. You’ll find the crowds since everyone comes to the park.

The Chicago Cultural Center and the Art Institute are also located here.

Grant Park

Grant Park is the next stop for the Buckingham Fountain. The fountain is one of the largest in the world, known for its light displays and hourly water shows.

Palmer House Brownie Stop

Before leaving downtown, stop inside the historic and jaw-dropping Palmer House and grab the original Palmer House Brownie from the pickup express area.

The world’s first brownie is a mix of fudge and a regular brownie, making it the perfect afternoon treat. The Palmer House is a fantastic place to stay.

If you are ready for dinner, Berghoffs is a short walk away and offers incredible food and old-fashioned waiters.

Evenings in Chicago

Head back to your hotel for a short break before dinner. Then choose one of two great Chicago evenings:

Option 1: Wrigley Field

Catch a Cubs game for one of baseball’s most iconic stadium experiences. It’s a few miles outside of downtown, so plan to Uber for 20 minutes. Most people plan their entire trip around home games. The atmosphere and the fans are worth every effort. Field tours are also available most days.

I learned the hard lesson that Chicago heat can be as brutal as Alabama’s, with a sweltering heat index of 101 degrees during our 1 pm game day. If Wrigley Field is why you are coming, plan two home-game options. That gives you flexibility to pivot if weather affects the game.

Other sport options:

• White Sox Baseball Game
• Chicago Bears Football game (NFL)
• The Chicago Bulls (NBA)
• Chicago Blackhawks (NHL)

Free summer advice: Teenagers are not happy outside in 100-degree weather. They don’t care what you paid for tickets.

Option 2: Chicago Entertainment

Prefer a quieter evening? Book a Broadway show at the iconic Chicago Theatre, home of the famous CHICAGO marquee. The Auditorium Theatre has beautiful historic interior and is considered one of the grandest theatres in America. Then there’s the Goodman Theatre, James M. Nederlander, and the Cadillac Palace Theatre, and the list goes on for 200 more options.

For comedy, magic, and jazz performances try:

• The Second City is the best comedy show.
• Zanies Comedy Club has touring comedians.
• The iO Theater for improv and a younger crowd.
• Chicago Magic Lounge for a speakeasy style vibe.
• The Magic Parlour is an up-close, more elegant environment.
• The Magic Penthouse is a cocktail-party experience.
• Green Mill Cocktail Lounge is a famous jazz club with an old-school atmosphere.
• Andy’s Jazz Club has dinner and is located downtown.
• Kingston Mines is a legendary blues club with an energetic late-night atmosphere.

Let’s decide where to eat before our show.

Where to eat in Chicago?

• Gino’s East (pizza) & Portobellos (hot dogs) made my itinerary.
• Gene & Georgetti is Chicago’s oldest steakhouse with old-school charm.
• Au Cheval has the best burgers in America.
• Miru has stunning views of the river where it meets Lake Michigan, with Japanese cuisine.
• Tre Dita has elegant Italian dining with spectacular skyline views.
• Lou Mitchell’s is a Chicago breakfast diner institution and a traditional starting point of Route 66.
• Jim’s Original is a legendary street Polish sausage stand for a late-night snack.
  

Day 3: Lake Michigan & Lincoln Park

Morning: Navy Pier

Start your final day exploring the Navy Pier. Walk the waterfront, browse the shops, enjoy lake views, or take a 15-minute ride on the Centennial Wheel. This is a 3,000-foot-long space, so plan on a couple of hours.

For example, enter through the Polk Bros Park and stroll the South Boardwalk, ride the Centennial Wheel, the Flyover, stroll the Peoples Energy Crystal Gardens, pick up a bag of Garrett Popcorn, then snap a photo on the south dock edge.

Lunch at Portillos’s

Lunch at Portillo’s & Barnelli’s for famous hot dogs and chocolate cake. It’s about a mile walk.

Relax at the Beach

• Depending on the season, spend a little time along Lake Michigan’s shoreline.
• Even if you’re not swimming, the beaches offer beautiful skyline views and are a great place to unwind before heading home.
• You can walk the Lakefront Trail between the Navy Pier and Oak Street Beach.
• However, I’m a Florida girl, and these beaches were packed with people.

Lincoln Park Zoo

• Finish your Chicago weekend at Lincoln Park Zoo.
• One of the best parts? Admission is completely free.
• The zoo is beautifully landscaped and offers excellent skyline views nearby.
• However, I walked in circles trying to find the polar bear. I like zoos that flow in one direction, but this one doesn’t.

Brookfield Zoo

While we are talking about zoos, Chicago has the highly rated Brookfield Zoo, which is 18 miles outside of the city. The Brookfield Zoo has over 3,500 animals in a 216-acre suburban park.

If the weather doesn’t cooperate, swap the beach and zoo for one of Chicago’s outstanding museums. Honestly, I would choose The Art Institute of Chicago over the beach and the zoo if I were traveling without teenagers.

Chicago Museums

• The Art Institute of Chicago is a world-renowned museum filled with over 300,000 works of art across one million square feet of space. It costs around $30.

• The Field Museum is a world-famous history museum with 40 million artifacts, including SUE the T-Rex and Maximo the Titanosaur. Tickets cost around $30.
  

The Griffin Museum of Science

• The Griffin Museum of Science and Industry is one of the largest science museums in the world, complete with a WWII German submarine, Science Storms with a 40-foot water vapor tornado, and a 3,500 square foot model railroad track from Chicago to Seattle.

• The Shedd Aquarium features 32,000 animals including beluga whales, dolphins, a Caribbean reef, and penguins.
  
• The Chicago Cultural Center features the world’s largest Tiffany stained glass dome, stunning architecture, and rotating art exhibits. It’s located across from Millennium Park and is free.

Obama Presidential Center

• Obama Presidential Center is a 19-acre campus with a multi-story museum, an athletic facility, and green spaces.
• Driehaus Museum is one of the last Gilded Age mansions in Chicago.

7 Day Chicago Itinerary

By adding a couple of museums, a walking tour, Chinatown, and live-venue music, magic, or comedy events, it’s easy to stretch the Chicago vacation to seven days. Traveling with my guys, we are booking a Chicago fishing charter on Lake Michigan for salmon and trout.

Chicago Walking Tours

Chicago is one of the best walking cities in the U.S., and the guides are knowledgeable and fun.

• Chicago Mafia Walking Tour
• A Chicago’s Gangsters & Ghost Tours for Al Capone, speakeasies, and crime history
• Inside Chicago Walking Tour- goes inside famous buildings
• The Chicago Food & City Tours
• Chicago Architecture Center- Historic Loop Tour

Visit the Hyde Park Neighborhood

Hyde Park is a historic, diverse Chicago neighborhood known for the University of Chicago, beautiful architecture, and attractions like the Museum of Science and Industry, Robbie House, and Promontory Point. It offers a mix of academic institutions, parks, restaurants, and shops with a vibrant arts scene and lakefront access.

Let’s start the day with breakfast at the iconic 100-year-old Valois Cafeteria. Then pick an activity below.

Things to do near Hyde Park

• University of Chicago
• Museum of Science and Industry
• DuSable Museum of African-American History
• Smart Museum of Art
• Robbie House built by Frank Lloyd Wright
• Parks- Jackson, Washington, Midway Plaisance, and Promontory Point on Lake Michigan with skyline views.
• Court Theatre and Jazz Clubs

Medici & Shopping

Next, lunch at the Medici on 57th because it’s a neighborhood institution with burgers and milkshakes. After lunch, explore 57th Street Books, Powell’s Books, The Silver Room, and Hyde Park Records. Basically, shopping between 53rd and 57th Streets for independent boutiques. Then, walk to Promontory Point for the skyline views. Let’s end the day with dinner at the acclaimed Virtue Restaurant, serving up Southern-themed soul food in an elegant setting.

Chicago’s Chinatown

Today, we will experience neighborhoods with distinct personalities, which gives us a broader feel for Chicago beyond the basic loop.

• Let’s start the day in Chinatown with the Chinatown Gate.
• Chinatown Square
• Nine Dragon Wall
• The Chinatown murals
• Chinese shops
• Bubble tea shops
• Walk over to the Ping Tom Memorial Park for pretty skyline views of Chicago without the crowds.

Garfield Park Conservatory

After a couple of hours, take the Chicago Water Taxi from Chinatown to downtown. The next stop is the Garfield Park Conservatory, often called “Chicago’s hidden botanical garden.” You’ll see massive tropical plants, a desert house, a fern room, and seasonal flower displays.

Pilsen Neighborhood

Last stop of the day is the Pilsen Neighborhood in one of Chicago’s coolest neighborhoods. The highlights are incredible murals, coffee shops, boutique shopping, and Mexican art galleries along 18th Street. End the day with dinner at HaiSous Vietnamese Kitchen, 5 Rabanitos Restaurant, or Carnitas Uruapan.

Where to Stay in Chicago

Palmer House Hilton

• If you love historic hotels with classic Chicago charm, the Palmer House is impossible to beat.
• Its central location makes walking to Millennium Park, the Theatre District, and many downtown attractions incredibly convenient.
• The fact that it serves famous brownies all day is just a bonus.
• If the Palmer House is booked, then I’m headed to the Riverwalk.
• I would skip VRBO’s in a neighborhood due to traffic.

Hotels Along the Chicago River

If waking up to skyline and river views is more your style, consider staying near the Chicago Riverwalk. These hotels provide easy access to architecture cruises, restaurants, and many downtown attractions.

Great options include:

• LondonHouse Chicago – for the skyline views
• The Langham, Chicago
• Renaissance Chicago Downtown Hotel
• Sheraton Grand Chicago Riverwalk
• Hyatt Regency Chicago
  

When to visit Chicago

• October has Open House Chicago, where dozens of historic buildings open to the public with information from the Chicago Architecture Center.
• Baseball season for Wrigley Field games.
• Chicago has an average of 8 street festivals per weekend.
• September, October, April & May are the best months for pleasant walking weather and smaller crowds.

My kind of town, Chicago is.

Frank Sinatra

Three days is just enough time to fall in love with Chicago. Between the world-famous architecture, incredible food, beautiful lakefront, and endless entertainment, it’s easy to see why I planned a return visit before I even left.

Thank you for reading my Chicago Weekend Itinerary. You are the BEST!

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