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Looking to plan the best 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 for a fantastic visit to Chi-town!
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 Chicago attractions are found in the very walkable downtown, but a few must-see Chicago sights are scattered further afield. We are sharing our top tips and a day-by-day Chicago 3-Day Itinerary so that you can plan a Chicago trip without worry free.
Pro Tip: Get (and stay) organized for your vacation to Chicago using our Trip Planning Printables!
3 Days in Chicago
Chicago is one of the best weekend destinations in the United States! 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 our perfect Chicago 3 Day Itinerary.
In fact, our trip plan is designed for a long weekend in Chicago – based on the assumption that visitors will arrive on Friday or Saturday and stay until Sunday or Monday. 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.
What To Eat & Drink during your Chicago 3 Day Itinerary
Eating is one of the top things to do in Chicago in 3 days. The city is home to numerous legendary eateries – far too many to fit into one fun weekend trip in Chicago. To help, we have narrowed it down to the best Chicago food options.
Throughout our Chicago Three Day Itinerary, we highlight the most famous Chicago restaurants. Our food recommendations include classic eateries, Chicago’s best hot dogs, and – of course – iconic Chicago deep-dish pizza. For drinks in the Windy City, we feature locally brewed beer, swanky cocktail lounges and famous jazz bars.
You will find all of our recommendations for food and drink sprinkled throughout our 3 Days in Chicago Itinerary.
Our Chicago Itinerary for 3 Days
Our 3-Day Itinerary for Chicago features the best of the city in an easy to follow day-by-day plan. 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 everything you need to plan your ultimate trip to the Windy City. Save, Bookmark or Pin this post for planning your Chicago trip!
Day 1 of Your 3 Day Chicago Itinerary: City View, Park, Beach and West Loop
On the first day of your 3-day trip to Chicago, get settled into your accommodations (recommendations below) – then get an overview of the city. Next, explore the city’s best park and beach before setting off for a fun night in Chicago’s West Loop.
360 Chicago Observation Deck
Start your Weekend in Chicago Itinerary with the city’s best view! Zip to the top of 875 North Michigan Avenue– formerly the John Hancock Center – to the 360 Observation Deck. The elevator ride only takes 40 seconds to travel 1,000 feet – so you should have no problem fitting the activity into your Chicago, Illinois trip plan.
Inside the 360 Observation Deck, visitors are greeted with incredible views of the Chicago skyline and Lake Michigan. Spend some time leisurely soaking in the view, sipping a drink at the bar or experiencing the thrilling TILT. Buy your tickets now!
Lincoln Park, Lincoln Zoo and North Avenue Beach
With your feet back on the ground, explore the myriad of paths that crisscross through the expansive lakeside Lincoln Park. If you are planning a trip to Chicago with kids, don’t miss the Lincoln Zoo (it’s free!)! If the weather is cooperating, continue your walk on the sand at North Avenue Beach – and if it’s summertime, consider taking a swim in Lake Michigan.
Deep Dish Pizza for Lunch
For lunch, indulge in the city’s most loved culinary creation: Deep Dish Pizza. Lou Malnati’s Pizzeria is a Windy City favorite known for their butter crust – and is a must-try during your 3 days in Chicago. The family-owned restaurant has several city locations (including one just south of Lincoln Park).
That said, it’s not the only place to get gooey deep dish deliciousness on your weekend Chicago trip. There are dozens of highly acclaimed pizzerias serving up deep dish pies in Chicago. Giordano’s, Pizzeria Uno and Gino’s East are all good options for Chicago deep dish pizza. The Chicago Pizza and Oven Grinder Company, however, gets our vote and many rave reviews for their deep dish pizza and creative Pizza Pot Pies.
Goose Island Fulton Street Brewery Tour
After lunch, continue to the next stop on your Three Days in Chicago Itinerary: 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 brewery tour to witness the behind-the-scenes production process…and then sip delicious, fresh beer. Even if you skip the tour, this is a fun brewpub for a beer and should definitely be included in your three day Chicago itinerary!
Time Out Market Chicago
We were first introduced to the concept of Time Out Markets in Lisbon, Portugal, where we were absolutely thrilled that they brought 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, the concept is the same – and we think it’s a must for your Chicago Itinerary.
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.
A Night Out during Your 3 Day Itinerary Chicago
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 the West Loop (or beyond).
Best Bars for Day 1 of your 3 Days in Chicago
There is no shortage of hip hangouts in West Loop, so where you go depends on your taste! To help you decide, we’ve rounded up a short list of some of the fun bars you can add to Day 1 of your Chicago 3 Day Itinerary.
Just a block west of the Time Out Market is Blind Barber, a barbershop by day…and a swank, 70s-style speakeasy by night.
Emporium Fulton Market
The fun Emporium Fulton Market is just down the street to the east – and features an array of arcade games and good cocktails.
Lone Wolf Chicago
A favorite neighborhood spot, the Lone Wolf is a classic and comfortable establishment to start off your night.
If you are in search of Chicago craft beer, don’t miss Haymarket Pub and Brewery. They also feature live music on weekends.
Green Mill Cocktail Lounge
However, visitors who are planning a trip to Chicago and 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 prepared; it’s a bit north of the city, there is a cover charge, it’s cash only and seating is first come, first served.
Day 2 of Your Chicago Itinerary in 3 Days: The Loop, Architecture and Windy City 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!
Breakfast At The Famous Lou Mitchell’s
For breakfast on Day 2 of your Chicago trip, 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 Chicago must!
Union Station Chicago
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 Hollywood films including The Untouchables and My Best Friend’s Wedding.
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. Exploring this area is an absolute must when visiting Chicago.
Trip Planner Chicago Loop
Begin your discovery 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 Chicago (be sure to buy your ticket in advance!). After visiting the Willis Tower, continue on your tour of the Chicago Loop.
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 and Grant Park (Cloud Gate mirrored sculpture a.k.a. The Bean, 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)
- 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. This iconic eatery is surely a highlight of any weekend trip to Chicago.
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 original owner was the historic instigator of the Chicago 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 Chicago skyline – it’s an absolute must for your Chicago weekend itinerary. Enjoy an entertaining hour-long river 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 Chicago Cubs (unless you’re from the South Side or St. Louis), Wrigleyville is a north side neighborhood packed with lively bars and fantastic eateries. The historic Wrigley Field is at the heart of the neighborhood – and attending a baseball game (regardless of who you’re rooting for) 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 the Cubby Bear or Casey Morans – for pub grub and drinks or go for an upscale dinner at Mordecai.
Alternatively, if seeing a baseball 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 sports events that you could add to your three days in Chicago trip plan. Check schedules for the world famous Chicago Bulls (basketball), Chicago Bears (football), Chicago Blackhawks (ice hockey) and Chicago Fire (soccer).
Day 3 of Your Weekend in Chicago Itinerary: Walking Trail, Hot Dogs & Navy Pier
Wrap up your 3 Days in Chicago Itinerary with more sightseeing, eating and walking it off! 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.
Walk Off the Food You’ve Eaten in Chicago in 3 Days
If you are going to plan a trip to Chicago that includes gorging on the local fare, then you should also carve out some time to walk off all the calories. While our Weekend in Chicago Itinerary naturally includes a lot of walking between sights, there are two fabulous places to hit the trails in the city: 606 Bloomingdale Trail and Lakefront Trail.
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. Pop into Mindy’s Bakery, run by famed Chicago chef Mindy Segal, for an incredible breakfast before starting your walk.
As the name suggests, the Lakefront Trail fronts Lake Michigan. The trail stretches for 18 miles and can be used by bicyclists and pedestrians. From the path, there are fabulous views of Chicago and the shoreline. Hop on at any point and walk as far as you would like!
Famed Chicago-Style Hot Dogs
Your Chicago Trip Planner is not complete without consuming at least one hot dog. Chicago dogs are noted for being ‘dragged through the garden’ – meaning, piled high with toppings that include mustard, onions, relish, tomatoes and a dill pickle spear sprinkled with celery salt (but never ketchup!). Unarguably, the place to get a hot dog is at Portillo’s – a long-time, well-known chain that originated in the city (and has now expanded across the United States).
In addition to hot dogs, Portillo’s also serves fabulous Italian Beef Sandwiches – another must-eat in Chicago! However, if you are just going after the beef, then go to Al’s #1 Italian Beef – an eatery that was established in the city in 1938.
Alternatively, Join a Chicago Food and Drink Tour
While we have included some of the top must-eat restaurants in our Chicago in a Weekend Itinerary, there is still more feasting to do! Rather than choosing one place for lunch on the last day of your 3 perfect days in Chicago, taste-test your way through the city. Join an expert guide in the local foodie scene to discover favorite haunts and classic fare including Deep Dish Pizza, Italian Beef, famous Chicago Hot Dogs and more. Get the details here!
Navy Pier Chicago
Complete your Weekend in Chicago Itinerary with a leisurely afternoon on Navy Pier. Like Pier 39 in San Francisco, Navy Pier caters to tourists – but in a fun way that doesn’t disappoint! Featuring an array of restaurants, souvenir shops and art exhibitions, Navy Pier is a must-see in Chicago…and a great way to end your Chicago 3-Day 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 to chic boutiques – and is a top destination for fashionistas planning a 3 Days in Chicago Itinerary.
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 to include on your Chicago trip itinerary!
Chicago Trip Ideas: What Museums to Visit
When you plan trip to Chicago, it can be difficult to choose which museums to visit on your vacation. We are highlighting a few of the city’s most renowned museums to help you decide.
Art Institute of Chicago: The city’s most famous art museum, the Art Institute is a top pick for 3 days in Chicago trips (buy Skip-the-Line Tickets!).
Museum of Science and Industry: The hands-on, family-friendly Museum of Science and Industry is a good museum to visit if you are planning trip to Chicago with kids.
Museum of Contemporary Art: The fun and modern Museum of Contemporary Art is a fantastic museum to visit on a weekend getaway to Chicago.
Shedd Aquarium: Whether traveling with kids, as a couple or with a group of friends, the state-of-the-art Shedd Aquarium is a good addition to your Chicago vacation planner.
The Field Museum: A fascinating museum of mummies and dinosaurs, the Field Museum is an excellent stop on a 3 day trip to Chicago.
Adler Planetarium: If time permits in your itinerary, plan a day in Chicago that includes stargazing at the Adler Planetarium.
Pro Tip: Save money and skip lines with a Chicago CityPass! If you are planning on visiting more than one museum during your three days in Chicago, it will almost definitely save you money!
Go to a Theater Performance in Chicago
Need more ideas of what to see in Chicago in 3 days? Go to a show! 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.
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 in Chicago are Chinatown, Little Italy, Lincoln Park, Wicker Park, Boystown and Roscoe Village.
How Many Days in Chicago?
We think 3 days in Chicago is the perfect amount of time to get acquainted with the city…but we would have no problem entertaining ourselves for a week in Chicago!
How many days you spend in Chicago will ultimately depend on your interests, budget and available time.
Sample Chicago Itineraries
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!
Chicago 1 Day Itinerary Trip Plan
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 instead.
Chicago Itinerary 2 Days
With 48 hours in Chicago, visitors can plan a Chicago 2-Day Itinerary that is succinct and hits almost all of the highlights.
Chicago 2 Day Itinerary Trip Plan
If you are planning a 2-Day Itinerary for Chicago, we suggest following 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, even squeezing in the Goose Island Brewery Tour if possible.
Chicago Itinerary 4 Days
Planning a 4-Day Chicago Itinerary allows for a lot more sightseeing – including many of the museums that we skipped in favor of neighborhood exploration.
Chicago 4 Day Itinerary Trip Plan
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.
Chicago 5 Day Itinerary Trip Plan
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 Your 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 to Chicago
An essential consideration for your Chicago trip itinerary is how to get there! Chicago can be reached by car, bus, train or plane. On our trips to Chicago, we have always arrived via plane.
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 (London, Hong Kong, Tokyo, Munich, etc.), but is far from the city center. Alternatively, Midway services mostly US domestic flights, but is much closer to downtown Chicago.
Getting around Chicago
Downtown Chicago is very walkable – but getting to the districts outside the city center require transportation. Besides your own two feet, visitors have options when it comes to getting around Chicago – from the ‘L’ train to CTA buses to bikes to scooters to Uber and Lyft.
Chicago has one of the most extensive public transportation systems in America and makes getting around Chicago fairly easy. Both the ‘L’ train and buses have extensive networks. The affordable fares can be paid using a Ventra account – and both 1-Day and 3-Day flat fare tickets are available. Find fare info here.
More Ways to Get Around Chicago
That said, using Uber or Lyft is likely much more convenient – and if traveling in a group – not too expensive.
We do not recommend driving a car during your Chicago weekend itinerary; 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 the hotel amenities that are most important to you – and use the map to find the best location. Be sure to read all of our best tips for booking hotels!
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. However, this is not always true on short stays. Be sure to check the extra fees when booking a short trip – like 3 days in Chicago – before confirming your Airbnb stay.
What To Pack For Your Chicago Trip
We have a few tips and packing hacks for what to pack for your 3 perfect days in Chicago.
Weather Appropriate Clothing for Your Chicago 3 Day Itinerary
What you pack in your suitcase for a 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. So yes, 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 and carry a great day bag for quick wardrobe changes.
Walking Shoes for Your Itinerary for Chicago
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 three days in Chicago. 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 budget camera for beginners!
US Travel Insurance
We think travel insurance is essential for any trip – even a long weekend in Chicago. It can cover unfortunate situations, like cancelled trips, lost luggage and more. Check rates and coverage on World Nomads.
Visit More Top Destinations In The USA
Planning other trips in the United States? Use our detailed guides to help you discover the best of cities across America. In fact, we wrap up our top picks for the best places to go in our guide, 22 Weekend Getaways in the US!
Find all of our tips for traveling in the United States on our USA Travel Destinations Page.
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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