Chicago Itinerary

A complete 3 day Chicago itinerary to help you plan your visit to the Windy City! All the must-see sights, things to do, and restaurants to try.

I’ve lived in Chicago for nearly 12 years and I have a strong love of this city. Over the past several weeks I have shared in-depth Chicago neighborhood guides and today I am pulling my top Chicago recommendations together into a 3 day Chicago itinerary.

With this itinerary I have grouped together activities that are located near each other and work together well logistically. I’m listing more than necessary to fill each day because I want to give you options – choose your own adventure!

When to Visit Chicago

Table of Contents

The best time to visit Chicago is between May and September. The winters are brutally cold and the city comes to life during the warmer months. In July and August it can be very hot, while the weather is milder in May, June, and September.

Map provided by Wanderlog, a road trip planner

The idea is that you can walk between most of the destinations on these itineraries – so pack comfortable shoes!

Chicago Itinerary Day 1: Downtown Chicago

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

Walk the Magnificent Mile

The Magnificent Mile is a mile long stretch of Michigan Avenue where you will find landmarks like the historic water tower, attractions like 360 Chicago – the Hancock Tower’s observation deck, Starbuck’s Reserve, and luxury shopping. The Mag Mile starts in the Gold Coast and ends at the Chicago River. For this itinerary to make the most sense, start in the Gold Coast and walk downtown.

The Architectural Boat Tour

Learn about Chicago history and architecture while cruising down the Chicago River. This tour is considered to be one of the best things to do in Chicago. The best tour is run by the Chicago Architecture Center.

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.

See Cloud Gate (the Bean), 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.

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 runs along the south side of the Chicago River. City Winery has a Riverwalk location and it’s a perfect spot if you want to stop for a happy hour drink.

Have Dinner

If you want to watch the fireworks, you might want to dine at Cindy’s Rooftop which has a great view of the fireworks. Or, you can grab dinner in River North and then make your way to Navy Pier for the fireworks. River North has many excellent dining options including RPM Italian, RPM Steak, RPM Seafood, Siena Tavern, Bavette’s Bar & Boeuf, and Frontera Grill.

Option 1: See the fireworks!

One of the best places to watch the fireworks is from Cindy’s Rooftop. You can also watch from Navy Pier which has a large rooftop bar. 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 (or late night): See Live Music

Both Andy’s Jazz Club and Buddy Guy’s Legends are located in downtown Chicago. You could also do this after the fireworks!

Option 3 (or late night): Check Out a Tiki Lounge

3 Dots and a Dash in River North is alway fun.

Chicago Itinerary Day 2: Lincoln Park and Lakeview

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

Brunch at Mon Ami Gabi

I love this elegant French restaurant on the edge of Lincoln Park.

Lincoln Park

After brunch, walk across the street to Lincoln Park, 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.

Lincoln Park Conservatory

This botanical garden within the park both 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. Chicago has over 20 miles of beaches along Lake Michigan and biking along the lake is one of my favorite summertime activities.

Option 1: Cheer for the Cubs

If you are a baseball fan, seeing a game at Wrigley Field is a must. It’s best to get tickets in advance – prices can vary depending on the quality of seats, time of year, and how well the team is doing.

Option 1 part 2: Grab a Drink or a Bite to Eat

If you need to eat before or after the game, Hotel Zachary has several excellent dining options. Big Star is a casual taco joint with wonderful tacos and margaritas, Smoke Daddy is a barbecue joint, Mordecai is a more upscale cocktail lounge serving American food, and Swift & Sons specializes in steak and seafood.

Option 1 part 3: Have a Nightcap at The Green Mill or Kingston Mines

The Green Mill is a jazz club that was one of Al Capone’s hangouts and it is still one of the best places to see live music in Chicago. It’s a little out of the way but it’s worth the effort to get there. Or, if you don’t want to venture north, head to Kingston Mines, one of the city’s best blues bars.

Option 2: Dinner in Lincoln Park

Sadly, there aren’t any restaurants that I love 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 my 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).

Option 2 part 2: 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. I recommend buying tickets in advance.

Option 2 part 3: 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, West Loop, and Old Town

This day starts off in the Wicker Park and ends in Old Town or the West Loop.

Brunch in Wicker Park

Cafe Robey, The Bongo Room, etta, Mindy’s HotChocolate, and Kanela Breakfast Club are all fine spots for brunch. If you aren’t super hungry, you can get a lighter breakfast at The Goddess and Grocer or a doughnut at Stan’s.

Explore Coffeeshops and Boutiques

I love Wicker Park because it is filled with independent coffeeshops and boutiques. The neighborhood is considered to be Chicago’s hipster neighborhood and it has a vibe all its own. When it comes to coffeeshops, I love Volumes Bookcafe which is half coffee house and half book store, and The Wormhole Coffee. If you want to browse the boutiques, stroll down Milwaukee Avenue from Damen to Division.

Happy Hour

Want a happy hour drink? Go to Queen Mary (opens at 5pm) or Violet Hour (opens at 6pm) for cocktails. If you want a place with a lively atmosphere where you can drink outside, go to Paradise Park.

Option 1: Have dinner in Wicker Park

Wicker Park has so many great restaurants. I recommend Dove’s Luncheonette (Tex-Mex), Big Star (tacos), Pub Royale (Indian), etta (Italian), and Mott Street (Asian).

Option 1 part 2: See a Show Second City

If you didn’t see a comedy show on Day 2, this is your chance. It’s about a 10-15 minute cab ride from Wicker Park to Second City which is in Old Town.

Option 1 part 3: Visit Old Town Ale House

After Second City, grab a drink at the beloved dive bar across the street. Heads up – it’s cash only. And if you want to bar hop, head to Wells Street.

Option 2: Dinner in the West Loop

Option two is to check out the West Loop, a neighborhood known for its restaurants. It’s a short cab ride from Wicker Park. One of the newest and best additions to the West Loop is the Time Out Market, massive food hall is home to mini versions of some of Chicago’s top restaurants. Try everything from deep dish pizza to steak here. You might want to also check out the rooftop bar.

If you prefer to dine at a restaurant, there are so many options. My top picks are Roister (American), Duck Duck Goat (Chinese), Girl & The Goat (modern American), The Loyalist (famous for their burger), Monteverde (Italian), Bar Siena (Italian), and Maude’s Liquor Bar (French). I’ll mention Au Cheval which is famous for its burger, but they don’t take reservations and the wait can be extremely long – you will have better luck going late night.

Option 2 part 2: A Night Out in the West Loop

After you eat, check out the West Loop’s nightlife! Aba is an elegant rooftop, 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.

Option 2 part 3: 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.