Chicago Itinerary: 7 Mix and Match Itineraries

A Chicago itinerary with seven days of sightseeing, museums, activities, and restaurants that can be mixed and matched based on your interests.

Each day of this Chicago itinerary was created with the idea that it is easiest to explore one or two neighborhoods in a day and to walk between most activities. Some days cover classic Chicago activities like the architecture boat tour, seeing a show at Second City, and catching a game at Wrigley Field. Other days are focused on letting you explore Chicago like a local. And, in case it rains or is too cold to spend much time outside, we created an itinerary for that too.

These itineraries are packed – it might be more than someone wants to do in one day. Pick and choose what interests you the most, or spend two days working through one of the itineraries.

Last updated: April 2022

The Chicago Itineraries:

Chicago Itinerary Day 1: Downtown Chicago

If you will be in Chicago during the summer, save this downtown Chicago itinerary for a Wednesday or a Saturday so that you can end the day by seeing the fireworks.

Walk the Magnificent Mile heading South

The Magnificent Mile is a mile long stretch of Michigan Avenue the connects the Gold Coast and Streeterville, ending at the Chicago River. The Mag Mile is home to landmarks including the Historic Water Tower, attractions like 360 Chicago – the Hancock Tower’s observation deck, Starbuck’s Reserve, and luxury shopping. For this itinerary to make the most sense, start in the Gold Coast and walk downtown.

The Architectural Boat Tour

The Chicago Architecture Foundation Center’s river cruise gives guests the opportunity to admire Chicago’s skyline while learning about architecture and history. This tour tops most lists of best things to do in Chicago. The ship departs from 112 East Wacker which is at the intersection of Michigan and the Chicago River, at the end of the Mag Mile. Be sure to book tickets in advance.

Lunch at The Purple Pig or Eataly

The Purple Pig is a small plates Mediterranean restaurant that is great for groups and Eataly is an Italian market/food hall. Both are great spots for lunch – Eataly has grab and go options if you are on a time crunch.

Cloud Gate (the Bean), Millennium Park, Buckingham Fountain, and Grant Park

The massive reflective sculpture in the shape of a bean that sits in Millennium Park is one of Chicago’s most recognizable landmarks. From there it is easy to walk to Buckingham Fountain in Grant Park.

Maggie Daley Park

If you have kids, Maggie Daley Park is the ultimate playground. It’s actually a series of playgrounds for children of different ages.

The Art Institute of Chicago

Chicago’s largest museum is right next to Grant Park and it’s a must-visit for any art lover. You might remember the museum from Ferris Bueller’s Day Off.

Walk the Riverwalk

The Riverwalk is a series of bars and restaurants that run along the south side of the Chicago River. These restaurants are a great spot for a happy hour drink.

Dinner

When it is time for dinner, walk to the north side of the river to River North. This neighborhood has many excellent dining options including RPM Italian, RPM Steak, RPM Seafood, avec, Siena Tavern, Bavette’s Bar & Boeuf, and Frontera Grill.

Option 1: Navy Pier Fireworks (seasonal)

The Navy Pier Fireworks take place on Saturdays and Wednesdays from May 28, 2022 through September 3, 2022. The Saturday fireworks are from 10 pm until 10:10 pm and the Wednesday fireworks are from 9 pm until 9:10 pm.

One of the best places to watch the fireworks is from Cindy’s Rooftop. You can also watch from Navy Pier which has a massive rooftop bar called Offshore. Or, take a nighttime fireworks cruise of Lake Michigan.

Option 2: See a Play

Check Broadway in Chicago to find a listing of plays and musicals taking place in Chicago while you will be in town.

Option 3: Jay Pritzker Pavilion

This amphitheater in Millennium Park hosts concerts, movie screenings, and other events during the summer.

Option 4 (or late night): See Live Music

Both Andy’s Jazz Club and Buddy Guy’s Legends are located in downtown Chicago.

Option 5 (or late night): Check Out a Tiki Lounge

3 Dots and a Dash in River North is a Tiki Lounge with excellent cocktails that is hidden away in a basement.

Chicago Itinerary Day 2: Lincoln Park and Old Town

This day involves spending time outside on the lakefront, seeing a cubs game, and going to an iconic jazz club.

Lincoln Park

Lincoln Park is Chicago’s largest park. Within the park you will find many gardens and ponds, plus the Lincoln Park Conservatory and the Lincoln Park Zoo which are both free. The Green City Farmer’s Market takes place on Saturdays and Wednesdays in Lincoln Park from April through October and is a fun place to grab a bite to eat.

Lincoln Park Conservatory

This botanical garden within the park showcases exotic plans and is used to grow plants that are planted in gardens throughout the park. 

Lincoln Park Zoo

This free zoo is home to many different species of animals from lions and tigers to farm animals. 

Bike the Lakefront Trail

Walk south towards North Avenue Beach where you can rent a bike, or grab a Divvy bike to cycle along Lake Michigan. Set off on the Lakefront Trail, an 18.5 mile long bike path that runs along Chicago’s beaches.

Dinner in Lincoln Park

Sadly, there aren’t any truly wonderful restaurants near Second City – but if you get dinner near the Armitage Brown Line Stop, it is easy to hop on the train to Sedgwick and get to Second City. Lincoln Park has many dining options, some of our favorites are Cafe B-Ba-Reeba (Spanish tapas), Summer House Santa Monica (California inspired), Stella Barra (pizza and pasta), Blue Door Farm Stand (healthy farm to table), and Athenian Room (Greek).

See a show at Second City

Chicago is known for its comedy clubs, and the most famous is Second City. This comedy club has multiple stages and shows. You can see improv, sketch comedy, or other comedy shows here. It is best to purchase tickets in advance.

Check Out an Iconic Dive Bar

Old Town Ale House is a classic cash-only dive bar right across the street from Second City on North Avenue. It’s a fun place to grab a drink either before or after a Second City show. If you want to stay out, there are many bars on Wells Street, which is a short walk from the Old Town Ale House.

Chicago Itinerary Day 3: Wicker Park and West Loop

This Chicago itinerary starts off in the Wicker Park, the chill hipster neighborhood where High Fidelity was filmed, and ends in the West Loop Chicago’s dining hotspot.

Start near the Damen Blue Line L Stop

Begin your day at or near the Damen Blue Line stop where Damen, Milwaukee, and North all intersect. From here you will work your way south.

Brunch in Wicker Park

Dove’s Luncheonette, The Bongo Room, etta, and Kanela Breakfast Club are all fine spots for brunch. For something lighter, you can get a grab and go meal at Goddess and Grocer, Foxtrot, or Stan’s Doughnuts. For exceptional pastries, you can’t miss Mindy Segal’s bakery that is opening at 1623 N Milwaukee Avenue (not open as of April 2022 but should be opening soon).

Explore Coffeeshops, Vintage Shops, Record Stores, and Boutiques

Wicker Park is a neighborhood that is filled with independent shops. Make stops at Prery Collective, Vintage Underground, Reckless Records, and continue down Milwaukee Avenue. Stop for coffee at one of the neighborhood’s 20+ coffee shops. If you want to add an activity to the mix you can play video games at Emporium or play 9 holes of indoor mini golf at Big Mini.

Chicago Brewery District

The Chicago Brewery District is located between Wicker Park and the West Loop so it’s an easy stop on the way to the West Loop. (You will want to take a taxi or to use a ride share service). If you want to try a variety of beers, visit District Brew Yards, a space shared for four local breweries. If you want a brewery tour, visit Goose Island.

Dinner in the West Loop

From the Brewery District, get a ride to the West Loop. There are dozens of top notch restaurants in the West Loop. You can read our complete West Loop Restaurant Guide here. If you don’t want to commit to just one restaurant, head to Time Out Market, a food hall with mini versions of some of Chicago’s best eateries.

If you prefer to dine at a restaurant, make sure you make a reservation in advance. Our top picks for West Loop restaurants are Roister (American), Duck Duck Goat (Chinese), Girl & The Goat (modern American), The Loyalist (famous for their burger), Monteverde (Italian), Bar Siena (Italian), and Trivoli Tavern (upscale American).

A Night Out in the West Loop

After dinner, explore the West Loop’s nightlife which has something for everyone. The Darling is a cocktail lounge with entertainment, Punch Bowl Social has bowling, games, and karaoke, Lazy Bird has a menu of 52 cocktails, and Lone Wolf is a casual spot with great drinks. If you want to see live music, check out who is playing at City Winery.

Get a Late Night Burger at Au Cheval

Chicago’s most legendary burger is hard to get. Sometimes the wait for a table is 5 hours long. If you happen to be out and about and hungry late at night, you might be lucky enough to get a table so you can feast on one of the best burgers you will ever have. As of April 2022, Au Cheval is open until 10:15 pm.

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Chicago Itinerary Day 4: Hyde Park

Hyde Park was the location of the 1893 World’s Fair. The neighborhood is filled with history, stunning parks, and incredible architecture.

Washington Park

If you want to take the L, get off at the Garfield Green Line stop. Then walk directly east to Washington Park. The Washington Park Arboretum, the Fountain of Time Sculpture, and the DuSable Museum of African American History are all located within this park.

DuSable Museum of African American History

The DuSable Museum is the nation’s oldest independent African American museum and is dedicated to exploring the African American experience and accomplishments. The collection includes over 15,000 paintings sculptures, printed works, and pieces of historical memorabilia.

Walk along the Midway Plaisance

This park connects Washington Park, the University of Chicago Campus, and Jackson Park.

Lunch at Plain Air Cafe

A French-inspired cafe that is right next to the Robie House.

Tour The Frederick C. Robie House

The Robie House in Hyde Park is a UNESCO Wold Heritage site and one of a handful of examples or Frank Lloyd Wright’s work in the Chicago-area. This home is considered to be one of the finest examples of Prairie Style Architecture, an American architectural style pioneered by Wright. The Frank Lloyd Wright Trust conducts several different guided tours of the house. Children under the age of 8 are not permitted on the tours.

Explore the University of Chicago Campus

Admire the architecture of the University of Chicago campus and make your way back to the Midway Plaisance and to Jackson Park.

Jackson Park

A large 550 acre park spanning the east of Hyde Park along Lake Michigan that was designed by Frederick Law Olmsted and Calvert Vaux who also designed Central Park. This park was the site of the 1893 World’s Fair and is home to the Museum of Science and Industries, the Osaka Garden, the Garden of the Phoenix, the “Golden Lady” Statue of The Republic, and Yoko Ono’s SKYLANDING.

Museum of Science and Industry

A massive museum with exhibits about space travel, farming, and transportation. While the museum is geared towards children, adults like to see the German U-boat. The museum’s building was is one the only buildings constructed for the 1893 World’s Fair that still stands today.

Dinner at Nella Pizza e Pasta

A pizzeria known for Neapolitan style pizzas that received a Michelin Bib Gourmand Award.

Chicago Itinerary Day 5: Baseball, Beer, and Jazz

This Chicago Itinerary combines three of the things that Chicago is most known for. This itinerary works best when you attend an early afternoon game at Wrigley Field. If that isn’t possible, start in Ravenswood, then head to Wrigley, and take the Red Line to the Green Mill after the game.

Explore the Southport Corridor

Take the Brown Line, get off at Southport, and head north. This area is packed with wonderful restaurants and shops. By heading north you will be working your way towards Wrigley Field which is just 0.6 miles from the Southport station. If you want to eat before the game, check out Tuco & Blondie, Crosby’s Kitchen, or Big Star (right next to the stadium). If you want to grab a drink before the game, there are lots of sports bars on Clark Street.

See the Cubs at Wrigley Field

Seeing a game at Wrigley is the ultimate Chicago experience. When picking tickets, you might want to opt for the 200, 300, 400, or 500 sections which are covered providing shade and protection from rain. If you are looking for a rowdy time, get bleacher seats.

Take the Brown Line to Ravenswood

After the game, make your way back to the Southport Brown Line and take the train north five stops to Damen which will put you right in the heart of Ravenswood.

Explore Malt Row

Malt Row is a series nine breweries, one distillery, and a winery located along the Ravenswood Industrial Corridor. The breweries have tasting rooms and some offer tours but as of April 2022 the tours were still on pause. If you need to eat dinner, stop at Cultivate by Forbidden Root or Half Acre which both have full restaurants. Few of the malt row breweries have kitchens. Read more about Malt Row here.

The Green Mill

It is just over a mile from Ravenswood to The Green Mill in Uptown. You could walk it, or use a ride sharing service. The Green Mill was an Al Capone hangout and one of the best place for live jazz music. The Green Mill has live music every night from 8 pm until midnight – expect to pay a cover charge of $10-20 a person. You might want to arrive early to make sure that you can get a seat.

Chicago Itinerary Day 6: Pilsen and Chinatown

Immerse yourself in two culturally diverse Chicago neighborhoods: Pilsen and Chinatown. These neighborhoods are located on opposing sides of the Chicago River south of the Loop. Pilsen is known for its large Mexican population while Chinatown is a booming neighborhood with dozens of Asian shops and restaurants.

National Mexican Museum of Art (closed Mondays)

This free museum is home to one of the nation’s largest Mexican Art collections; it spans history from ancient Mexico to today. The Nuestras Historias Stories of Mexican Identity exhibit highlights works from the Permanent Collection that tell diverse stories of Mexican identity in North America and features works from both sides of the border. The museum is also a cultural hub hosting theater, dance, music, and literary events.

Chicago Arts District Galleries and Street Art on 16th Street

The stretch of Halsted Street between 17th Street and Canalport in East Pilsen is filled with street art and is home to many galleries. Additionally, fifty murals can be found along the 16th Street railroad embankment between Halsted Street and Western Avenue

Tacos

Pilsen is home to many of Chicago’s best Mexican restaurants. You can find casual take out spots and full service restaurants. Read more in our guide to Pilsen restaurants.

Travel to Ping Tom Park

Chinatown’s Ping Tom Park is across the Chicago River from Pilsen – you might want to take a quick cab ride to get there.

Ping Tom Memorial Park

This 17-acre park with Chinese design elements has walking paths and is the location of the water taxi stop. During the summer, kayak rentals are available. After exploring the park, walk to Chinatown Square.

Chinatown Square

A large two-level outdoor pedestrian marketplace lined with shops, bakeries, and restaurants. Browse shops selling Asian snacks, candy, and drinks, check out the clothing stores, try bubble tea at one of the tea shops, and snack on dumplings before settling in for a meal at one of the many restaurants.

Try Bubble Tea

There are several places for bubble tea in Chinatown Square, the most popular is Joy Yee.

Chinatown Gateway

Follow the dotted red line that marks the path from Chinatown Square to the Chinatown Gateway – stop to see the Nine Dragon Wall on the way. The Chinatown Gateway is on South Wentworth Avenue and marks the entrance to Chinatown. Beyond the gate, this area is filled with shops and restaurants.

Have Dumplings

Depending on how hungry you are, you might want to stop at Qing Xiang Yuan Dumplings.

Dinner in Chinatown

There are dozens of Asian restaurants in Chinatown. See our guide to Chinatown restaurants here.

Water Taxi

The water taxi is the most scene way to travel north from Chinatown. The taxi runs seasonally and stops in Ping Tom Park. From Chinatown, the water taxi makes stops at Union Station/Ogilvie, The Riverwalk, Michigan Avenue, Chicago Avenue, and Goose Island.

Rainy Day Chicago Itinerary:

When it rains in Chicago, it really rains. The city also tends to be quite cold for over half the year. There are times when you just don’t want to be outside. This Chicago itinerary takes that into consideration and includes several unique to Chicago activities that will keep you warm and dry. You might be tempted to visit Skydeck or 360 Chicago since those are inside activities, but it is best do those things on days when it isn’t cloudy so that you can really enjoy the full skyline view.

Eat First

The food options on Museum Campus aren’t great, so you will want to eat first. If you want to grab a bite near Museum Campus, MingHin Cuisine (the South Michigan Ave location), The Chicago Firehouse, and Little Branch Cafe are nice options.

Museum Campus

Three of Chicago’s top museums all share a campus: the Field Museum, the Shedd Aquarium, and the Adler Planetarium. It is best to pre-book your tickets.

Field Museum

Chicago’s famous T-Rex, Sue, can be found at this natural history museum along with cultural collections and anthropological artifacts from all over the globe. This museum has exhibits that visitors of all ages will enjoy, including young children.

Shedd Aquarium

Chicago’s aquarium is home to a wide range of animals including dolphins, penguins, sharks, sea otters, and more.

Adler Planetarium 

This was America’s first planetarium, and it’s the place to learn about astronomy and astrophysics. The planetarium has shows geared towards children (one involves Big Bird and Elmo) plus programming for adults. Each Wednesday, the planetarium is open until 10 pm for Alder at Night.

Punch Bowl Social

A 30,000 square food bar, restaurant, and entertainment center with a bowling alley, bocce, ping pong, karaoke, and a variety of games. The space turns 21+ at 10 pm but until then all ages are welcome.

Time Out Market

For dinner, head to Time Out Market in the West Loop. Start at the bar, go somewhere else to grab an appetizer, maybe try main courses from different restaurants, then head to the roof with dessert and have one last drink. Some favorite food stalls include Urbanbelly, Mini Mott, Big Kids, and Arami.

Lazy Bird or City Winery

If you want to end your evening with live music, head to Lazy Bird or City Winery. Lazy Bird is a cocktail lounge in the basement of The Hoxton hotel with live music Thursdays – Saturdays. Lazy Bird is about a block from Time Out Market. Chicago Winery is 0.5 miles from the Time Out Market – still walkable but maybe not if it is pouring. There is live music nearly every night, it is best to pre-book tickets.