3 Days in Chicago Itinerary How To Plan a Chicago Trip by JetSettingFools.com

3 Days in Chicago Itinerary: How To Plan a Chicago Trip

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Want to plan a trip to Chicago, Illinois? Don’t stress – we have it covered! After visiting the Windy City on numerous occasions, we have created the ultimate 3 Days in Chicago Itinerary. Including the best city sights, must-do activities and local eats, our Chicago trip planner is all you need.


How to Plan a Trip to Chicago, Illinois

Planning a Chicago trip can feel overwhelming, but we are here to help! Chicago is steeped in riveting history, decorated with dazzling architecture and is famous for its food scene. While Chicago is bordered on the east by Lake Michigan, the city sprawls in all other directions. Many of the top attractions are found in the very walkable downtown, but a few must-see sights are scattered further afield.

We are sharing our top tips and a day-by-day Chicago 3-Day Itinerary so that you can easily plan a Chicago trip without worry or stress.


3 Days in Chicago

Visiting Chicago in 3 days is just enough time to see the highlights and get a taste of the city – and we squeeze just about all that we can into a perfect Chicago 3 Days Itinerary. In fact, our trip plan is designed for a long weekend in Chicago – based on the assumption that visitors will arrive on Friday/Saturday and stay in the city until Sunday/Monday evening. That said, our Chicago in 3 Days Itinerary can be used for trips to the city on any days of the week (with just a few minor adjustments).

While we think three days in Chicago is a perfect amount of time to spend in the city, we know not all travelers are planning a 3-day Chicago trip. Therefore, we offer alternate Chicago itineraries – for shorter and longer trips – at the end of this post. Whether you are planning a 2-Day Chicago Itinerary, making plans for 4 days in Chicago or devising a Chicago 5-Day Itinerary trip plan, you can use our suggestions to plan your vacation.


Chicago Itinerary 3 Days: Day by Day

Our 3-Day Itinerary for Chicago features the best of the city in an easy to follow day-by-day plan. In addition to what to see and do, we also include recommendations for what to eat. At the end of the post, you will also find our tips for how to get there, where to stay and what to pack.

Our Chicago three-day itinerary includes absolutely everything you need to plan your ultimate trip to the city. Save, Bookmark or Pin this post so that you can use it while planning – and during! – your trip!


Day 1: Night on the Town in West Loop

On the first day of your 3-day trip to Chicago, get settled into your accommodations (recommendations below!) – then set off for a fun night on the town in West Loop.

Chicago Itinerary by JetSettingFools.com


Goose Island Fulton Street Brewery Tour

Kick off your Three Days in Chicago Itinerary at the Chicago-born Goose Island Brewery. Established as a small city brewpub in 1988, Goose Island is now a recognized beer brand across the United States and abroad. At the Fulton Street Brewery and Taproom, patrons are invited to take a tour to witness the behind-the-scenes production process…and then sip delicious, fresh beer.


Time Out Market Chicago

When we visited the first Time Out Market in Lisbon, Portugal, we were absolutely thrilled by the concept of bringing the best city chefs under one roof. At the Chicago Time Out Market, which is situated in the heart of the West Loop dining district, visitors can order dishes from any of the carefully selected 18 Chicago chefs. The warehouse-style market encompasses 50,000 square feet of dining space – and includes 3 bars and a rooftop terrace. The buzzing market features Chicago classics, international fare and decadent desserts that are all well-recognized brands of the city.


After Dinner Drinks

While patrons can linger at the Time Out Market bars, with only a weekend in Chicago, we recommend moving on to one of the hip bars in West Loop (or beyond!).

Honestly, there is no shortage of hip hangouts in West Loop, so where you go depends on your taste! Just a block west of the market is Blind Barber, a barbershop by day…and a swank, 70s-style speakeasy by night. The fun Emporium Fulton Market is just down the street to the east – and features an array of arcade games and good cocktails. A favorite neighborhood spot is Lone Wolf and, if you are in search of craft beer, don’t miss Haymarket Pub and Brewery.

However, visitors who want to sip a cocktail inside a Chicago institution should leave the West Loop and head uptown to Green Mill Cocktail Lounge. The iconic bar opened in 1907, was partly owned by Al Capone during Prohibition, has hosted famous singers – such as Billie Holiday – and now regularly hosts jazz and poetry nights. Just be aware, there is a cover charge, it’s cash only and seating is first come, first served.


Day 2: The Loop, Chicago Architecture and Sports

On the second day of your Chicago in a Weekend Itinerary, explore the city’s top attractions on foot and by boat, then end the day in a classic northside neighborhood, hopefully watching a baseball game!

How To Plan a Chicago Trip by JetSettingFools.com


Breakfast at the Famous Lou Mitchell’s

For breakfast, indulge in a hearty Midwest-style meal at the iconic Lou Mitchell’s. For almost 100 years, the diner has been serving up omelets and pouring coffee for hungry patrons. Definitely old school and a little quirky (they hand out Milk Duds), eating at Lou Mitchell’s is a must!


Union Station

Ease into your full day of Chicago sightseeing at the city’s landmark Union Station. Opened in 1925, the station serves Amtrak and Metra commuter lines – and ranks as the busiest rail station in the United States outside of New York City. Occupying an entire city block, the classic Great Hall waiting room is at the center – and is recognizable from many popular films.


The Loop Walking Tour

Spend the rest of the morning walking off your Midwest breakfast on a self-guided walking tour of the Chicago downtown Loop. The area is dominated by historic architecture, lush parks and intriguing artworks.

Begin at the well-recognized Willis Tower (formerly the Sears Tower), which ranked as the tallest building in the world when it was completed in 1973. Visitors can soar to the 103rd floor Skydeck (be sure to buy your ticket in advance!), but we prefer the 360 Chicago Observations Deck in the Hancock Building (which we visit on Day 3!). 

Explore the following Chicago Loop sights (in order) and use this link to Google Maps for locations.

Daley Plaza (and Picasso’s Untitled artwork), Miro’s Statue, Chicago Theater (and famous Chicago sign), Old Marshall Field Building (and legendary clocks), Chicago Cultural Center (and Tiffany Dome), Millennium Park (Cloud Gate mirrored sculpture, Crown Fountain – then detour out of the park to see the historic Route 66 Begin sign and go one block west to see the famed Palmer House Hilton Hotel – Chicago Stock Exchange Arch, Buckingham Fountain), Queen’s Landing, Lakeshore Trail (or north through park), Chicago Riverwalk (see The Wrigley Building and Tribune Tower across river) and DuSable Bridge.


Billy Goat Tavern for Lunch

End the tour by crossing the DuSable bridge and walking north on Michigan Avenue to the Plaza of the Americas – then have lunch at Billy Goat Tavern. Established in 1934, the Billy Goat Tavern opened at the Lower Michigan Avenue location in 1964 and has been serving their famous “Cheezborgers” ever since. The owner is the historic instigator of the Cubs’ Curse of the Billy Goat and the tavern was featured as the Olympia Cafe in 1960s Saturday Night Live sketches.


Chicago Architecture River Cruise

After lunch, hop on a boat for a different perspective of the city skyline. Enjoy an entertaining hour-long cruise along the three branches of the Chicago River. The on-board tour guide shares the history of the city and more than 40 buildings that you will pass along the way. Book your seat now!


Wrigleyville (and a Cubs Game)

Home to the much-loved (unless you’re from the South Side or St.Louis) Chicago Cubs, Wrigleyville is a north side neighborhood packed with lively dive bars and fantastic eateries. The historic Wrigley Field is at the heart of the residential neighborhood – and attending a baseball game is a highlight of any itinerary for Chicago!

If the Cubbies are not playing, it is still worth visiting the neighborhood for dinner and drinks. Visit one of the famous Clark Street sports bars – like Cubby Bear or Casey Morans – or go for an upscale dinner at Mordecai.

Alternatively, if seeing a game is at the top of your list of things to do in Chicago, then check the South Side White Sox schedule. Outside of the summer baseball season, the city hosts other pro teams – like the world famous Chicago Bulls basketball, Chicago Bears football, Chicago Blackhawks ice hockey and Chicago Fire soccer.


Day 3: Walking Trail, Famous Food, Observation Deck & Navy Pier

Wrap up your 3 Days in Chicago Itinerary with more sightseeing, eating and relaxing! Start the day at a cool urban park, embark on a local food tour, get a birds’ eye view of the city and end your Chicago tour itinerary at tourist hotspot, Navy Pier.

3 Days in Chicago by JetSettingFools.com


The 606 Bloomingdale Trail

Similar to the New York City Highline and the Paris La Promenade Plantee, the Bloomingdale Trail – part of The 606 – is a repurposed elevated train track-turned-public-park. Running three miles through four districts (Wicker Park, Bucktown, Humbolt Park and Logan Square) on Chicago’s northwest side, the walking trail features art installations and hosts local events. We recommend walking the trail from east to west. Churchill Field Park is a great place to hop on the trail – just pop into Mindy’s Bakery, run by famed Chicago chef Mindy Segal, first for an incredible breakfast.


Food and Drink Tour

While we have included some of the top must-eat restaurants in our Chicago in a Weekend Itinerary, we are not done feasting yet! For lunch, taste-test your way through the city. Join an expert guide in the local foodie scene to discover favorite haunts and classic fare, like Deep Dish Pizza, Italian Beef, famous Chicago Hot Dogs and more. Get the details here!


360 Chicago Observation Deck

After a lunch of Chicago classics, zip to the top of 875 North Michigan Avenue– formerly the John Hancock Tower – to the 360 Observation Deck. The elevator ride only takes 40 seconds to travel 1,000 feet. Inside the Observation Deck, visitors are greeted to 360-degree views of the city skyline and Lake Michigan. Spend some time leisurely taking in the viewpoints, sipping a drink at the bar or experiencing the thrilling TILT. Buy your tickets now!


Navy Pier

Complete your Weekend in Chicago Itinerary with a trip to Navy Pier. Like Pier 39 in San Francisco, Navy Pier caters to tourists – and it doesn’t disappoint! Featuring an array of restaurants, souvenir shops and art exhibitions, Navy Pier is a must-see…and the perfect way to end your trip!


More Chicago Things To Do

We have outlined our best Chicago itinerary, including the top things to do when you visit Chicago in 3 days. However, how to plan a trip to Chicago will depend on your specific interests. Therefore, we are sharing more fun things to do in the city that you may want to add to your weekend trip to Chicago itinerary.


Shopping on The Magnificent Mile

Visitors who want to go shopping in Chicago will find there is no shortage of stores! The best place to shop in the city is on the famed Magnificent Mile, which is the section of Michigan Avenue that runs from the Chicago River north to Oak Street. The cosmopolitan street is lined with an astounding 460 retailers – from recognizable department stores and chic boutiques.


Chicago Museums

With more than 65 museums in Chicago, there is certainly something for everyone. Whether it’s art, history or science that piques your interest, you can find a museum in Chicago that will fits the bill! Some of the city’s most renowned museums are the Art Institute of Chicago (buy Skip-the-Line Tickets!), the Museum of Science and Industry, the Museum of Contemporary Art, the Shedd Aquarium and The Field Museum.

Pro Tip: Save money and skip lines with a Chicago CityPass!


Go to the Theater

Chicago has a vibrant theater district comprised of more than 250 theaters. From world-class productions to comedy acts, some of the best actors and comedians in the world have graced the stages in Chicago.


Neighborhood Exploration

One of our favorite things to do in any city is explore the unique neighborhoods and districts. Throughout our Chicago weekend trip itinerary, we have featured some of the top Chicago districts – but we by no means covered them all. Some of the other places to explore are Chinatown, Little Italy, Lincoln Park, Wicker Park, Boystown and Roscoe Village.


How Many Days in Chicago?

We have outlined a perfect plan for a long weekend in Chicago – but what if your trip plans include more (or fewer!) days? No worries! Using our 3-Day Chicago Weekend Itinerary as a base, we are sharing our best suggestions for longer and shorter trips to the city.


1-Day Chicago Itinerary

Planning a Chicago in One Day Itinerary is not easy! The city has so many iconic sights and delicious things to eat that it is difficult to pick and choose which ones to include in your Chicago trip plan. However, if one day is all you have, then we suggest making the absolute most of it!

For us, an ideal One Day in Chicago Itinerary would follow Day 2 in our above plan of what to do in Chicago in three days. However, unless you are passionate about baseball, rather than going to Wrigleyville we would recommend spending the evening on Navy Pier or in West Loop.


Chicago Itinerary 2 Days

With 48 hours in Chicago, visitors can plan a Chicago 2-Day Itinerary that is succinct and hits all the highlights. In fact, if we were planning a 2-Day Itinerary for Chicago, we would follow Days 2 and 3 of our outlined plan for what to see in Chicago in 3 days. Again, if the Cubs were not playing, we would skip Wrigleyville and instead spend the evening in West Loop.


Chicago Itinerary 4 Days

Planning a 4-Day Chicago Itinerary allows for a lot more sightseeing! To organize an ideal 4 Days in Chicago Itinerary, we would follow our Chicago 3-Day Itinerary – then, on the last day, we would use the CityPass to visit the city’s top museums, including The Art Institute, Field Museum, Shedd Aquarium and Museum of Science and Industry.


Chicago Itinerary 5 Days

Spending 5 days in Chicago allows for a lot more adventures at a somewhat more leisurely pace. To plan a perfect 5-Day Chicago Itinerary, we recommend following the above outlined Chicago 4-Day Itinerary – then, on the last day, spend the morning leisurely discovering a neighborhood, go shopping on the Magnificent Mile in the afternoon and attend a theater performance in the evening – then get a drink at the Lobby Bar in the posh Palmer House for a nightcap.


Tips for Planning a Trip to Chicago

Now that you know what to do in Chicago in 3 days, we have a few more essential tips for your trip!


How To Get There

An essential consideration for your Chicago trip itinerary is how to get there! Chicago can be reached by car, train or plane. On our trips to Chicago, we have always arrived via plane.

Start your search for the best airfare and flight times on SkyScanner!

There are two major Chicago airports: O’Hare International (ORD) and Chicago Midway (MDW). Both airports have their pros and cons – O’Hare is an enormous airport servicing flights from around the world, but is far from the city, while Midway services mostly domestic flights, but is much closer to downtown.

Both airports are connected to the city via public transport, but visitors can also use taxis, Uber or shared transport, too. 


Getting Around

Downtown Chicago is very walkable – but getting to the districts outside the city center require transportation. Chicago has one of the most extensive public transportation systems in America (but that really isn’t saying much!), which makes getting around fairly easy. That said, using Uber is also convenient – and if traveling in a group – likely not that expensive. We do not recommend driving a car in Chicago; parking is a hassle and can cost a bundle.

Chicago Hop On Hop Off

The Chicago Big Bus provides an excellent service for travelers who want to easily get from one tourist site to the next. The Hop On Hop Off Chicago buses are double-decker, open-air vehicles that make stops at all top attractions – and include informative on-board commentary! Buy your ticket!


Where To Stay in Chicago

Although there are hundreds of places to stay in Chicago, for your Chicago vacation itinerary, we recommend choosing downtown accommodations.

If you are going to splurge for 3 nights in Chicago, there is no better place than The Palmer House Hilton. The historic hotel, featuring a gorgeous lobby, is in a prime location within the Theater and Financial Districts near Millennium Park.

That said, there are hotels in Chicago that fit every budget and style! To find the perfect Chicago hotel for your stay, start your search on Booking.com – like we do! Use the filters to select that amenities that are most important to you – and use the map to find the best location.

Pro Tip: In our travels, we often use Airbnb to find affordable apartments in the places we visit. In fact, we have found that Airbnb is sometimes less expensive – and offers more space! – than most hotel rooms. If you are new to Airbnb, you can use this link to create your account and save money on your first stay!


What To Pack

We have a few tips for what to pack for your 3 perfect days in Chicago!


Weather Appropriate Clothing

What you pack for your trip to Chicago will depend on the season. Winters can be frigidly cold, summers are often unbearably humid, springtime is wet and autumn is likely to be brisk, hot or soggy. The frequent weather changes make planning what to pack for your trip a bit of a conundrum.

If you are taking a Chicago summer vacation, pack loose-fitting clothes, a wide-brimmed travel hat and sunscreen. In the wintertime, you will need a winter coat, hat and gloves. And, if traveling in the spring or fall, make sure to bring a packable raincoat and travel umbrella. Because the weather can fluctuate, it is best to pack clothing that can be layered.


Walking Shoes

Our Chicago 3-Day Trip Itinerary includes a ton of walking! We recommend wearing a pair of comfortable walking shoes for trekking around the city. I like to wear these lightweight shoes by Columbia and Kris prefers wearing his Merrell trail shoes for city walks.



Chicago is incredibly photogenic – and, if you are anything like us, you will be snapping a lot of pictures during your sightseeing adventures. Instead of using your cell phone camera to capture the sights, we recommend upgrading to a real camera. We travel with a DSLR Canon Rebel and use an everyday 18-135mm lens. The camera comes bundled with tons of accessories – so it is perfect for beginners!


Travel Insurance

We think travel insurance is essential for any trip! It can cover unfortunate situations, like cancelled trips, lost luggage and more! Check rates and coverage on World Nomads.


Start planning your trip to Chicago, Illinois! Search for the lowest airfares, the best accommodations and fun things to do…then start packing!  Want more travel planning tips? Head over to our Travel Planning page for more information and tips on traveling – and for country-specific information, take a look at our Travel Guides page!


Visit Other Top Destinations In The USA: We have detailed guides for Portland, Austin, Seattle, Denver, Boston and San Diego


We Want To Know: Do you have any advice on how to spend 3 days in Chicago? Is there anything you would add to our Chicago Itinerary? Give us your best tips on how to plan a Chicago trip in the comments below! 


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3 Days in Chicago Itinerary Plan a Chicago Trip by JetSettingFools.com

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