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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 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. The city is steeped in riveting history, decorated with dazzling architecture and is famous for its food scene.
Many of the top Chicago attractions are found in the walkable downtown loop, and a few must-see Chicago sights are scattered further afield.
We are sharing our top tips in a Chicago 3-Day Itinerary so that you can plan your trip without worry!
3 Days in Chicago
Visiting Chicago in 3 days is just enough time to see the highlights and get a taste of the city. We squeeze just about everything into our perfect Chicago 3 Day Itinerary.
Our trip plan is designed for a long weekend in Chicago. That said, our itinerary can be used for any days of the week with just a few minor adjustments.
Our Chicago Itinerary for 3 Days
This 3-Day Itinerary for Chicago features the best of the city in an easy to follow plan. You will also find all of our recommendations for food and drink sprinkled throughout our 3 Days in Chicago Itinerary.
At the end of the post, we provide tips for how to get there, where to stay and what to pack.
Save, Bookmark or Pin our Chicago Itinerary for your Windy City trip!
Day 1 of Your 3 Day Chicago Itinerary
On the first day of your 3-day trip to Chicago, get settled into your accommodations (recommendations below) – then get an overview of the area. 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 this 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 TILT – which claims to be the Highest Thrill Ride on the Planet. Buy tickets!
Chicago Water Tower, Lincoln Park and North Avenue Beach
With your feet back on the ground, see some of the highlights of the City of Chicago. The Water Tower still stands as a top Chicago landmark.
Built in the 1860s, it’s located on the famous Magnificent Mile. It is one of the few buildings that survived the 1871 Great Fire of Chicago.
Next up is the city’s best green space: Lincoln Park. Explore the myriad of paths that crisscross through the expansive lakeside space.
If you are planning a trip to Chicago with kids, maybe stop at the Lincoln Zoo. Either way, continue your walk on the sand at North Avenue Beach. If it’s summertime, consider taking a swim in Lake Michigan!
Deep Dish Pizza for Lunch
For lunch, indulge in Chicago’s culinary creation: Deep Dish Pizza. Lou Malnati’s Pizzeria is a Windy City favorite known for their butter crust. The family-owned restaurant has several 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.
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 Chicago-born Goose Island Brewery. Established as a small city brewpub in 1988, Goose is now a globally recognized beer brand (thanks in no small part to it’s acquisition by Anheuser-Busch in 2011).
At the Fulton Street Brewery and Taproom, patrons are invited to take a tour to witness the production process and then sip delicious, fresh beer.
Even if you skip the tour, this is a fun brewpub and should definitely be included on a beer-lovers three day Chicago Itinerary!
Time Out Market Chicago
We were first introduced to the concept of Time Out Markets in Lisbon, Portugal. At the Chicago Time Out Market, the warehouse-style venue encompasses 50,000 square feet of dining space – and includes 3 bars and a rooftop terrace.
The buzzing Time Out 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 we wouldn’t blame you for lingering at Time Out Market, with only a weekend in Chicago, we recommend moving on to one of the hip bars in the West Loop (or beyond).
Blind Barber
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 Arcade Bar
This fun spot is just down the street to the east – and features an array of arcade games and craft cocktails.
Lone Wolf Chicago
A favorite local neighborhood spot, the Lone Wolf is a classic and comfortable establishment to add to your Chicago night out.
Haymarket Brewery
If you are in search of more Chicago craft beer, don’t miss Haymarket Pub and Brewery. They also feature live music on weekends.
Green Mill Cocktail Lounge
Those 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 and was partly owned by Al Capone during Prohibition. It has hosted famous singers – such as Billie Holiday – and now regularly features jazz and poetry nights. Just be prepared; it’s cash only and seating is first come, first served!
Day 2 of Your Chicago Itinerary in 3 Days
On the second day of your Chicago in a Weekend Itinerary, explore top attractions on foot and by boat. Then end the day in a classic northside neighborhood, maybe even watching a baseball game!
Breakfast at Lou Mitchell’s
Begin with a hearty Midwest-style meal at the iconic Lou Mitchell’s. For a 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 landmark Union Station. Opened in 1925, the transit hub ranks as the busiest rail station in the US outside of New York City.
Occupying an entire city block, the classic Great Hall waiting room is at the center. It may be 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 breakfast on a self-guided walking tour of the Chicago downtown Loop.
The district features 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 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 (buy your ticket in advance). After soaking in the view, continue on your tour of the Chicago Loop.
Explore the following Chicago Loop sights (in order) and use this Google Map 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, Grant Park & Surrounds (Cloud Gate mirrored sculpture a.k.a. The Bean, Crown Fountain, historic Route 66 Begin sign, famed Palmer House Hilton Hotel, Chicago Stock Exchange Arch, Buckingham Fountain)
- Queen’s Landing
- Lakeshore Trail
- Chicago Riverwalk (view The Wrigley Building and Tribune Tower across the 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.
Settle in for lunch at Billy Goat Tavern. This iconic eatery is surely a highlight of any visit to Chicago. Established in 1934, the 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 the inspiration for the Olympia Café in 1970s Saturday Night Live sketches.
Chicago Architecture River Cruise
After lunch, hop on a boat for a different perspective of the Chicago skyline. We believe it’s an absolute must for a summer Chicago weekend itinerary!
Enjoy an entertaining hour-long river cruise along the three branches of the Chicago River. The on-board tour guide shares history of the city and more than 40 buildings that you will pass along the way. Book your seat!
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. 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 while you are vacationing in Chicago, it is still worth checking out the area. Visit one of the famous Clark Street sports bars – like the Cubby Bear or Sluggers – for simple grub and drinks (or go for a gastropub dinner at Mordecai).
If the Cubs are away and 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 baseball season, there are numerous pro sports events that you could add to your three days in Chicago trip plan. Including the world famous Chicago Bulls (basketball), Chicago Bears (football), Chicago Blackhawks (ice hockey) and Chicago Fire (soccer).
Day 3 of Your Weekend Chicago Itinerary
Wrap up your Chicago getaway with more sightseeing, eating and walking. Start off at a cool urban park then embark on a local food tour. Next, get a unique elevated view of the city and end your Chicago tour itinerary at Navy Pier.
Walk Off the Food You’ve Eaten in Chicago in 3 Days
When we plan a trip to Chicago that includes gorging on the local fare, we also carve out time to walk it off!
While our Weekend in Chicago Itinerary naturally includes a lot of strolling between sights, there are two fabulous places to really stretch your legs: 606 Bloomingdale Trail and Lakefront Trail.
The 606 Bloomingdale Trail
Similar to the Highline in NYC and the Paris La Promenade Plantee, the Bloomingdale Trail at 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 route features art installations and hosts local events. We recommend walking The 606 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 off. Just be warned, there will likely be a line out the door! Breakfast at Mindy’s is one of the top things to do in Chicago on a weekend – and it’s closed Monday – Wednesday.
Lakefront Trail
As the name suggests, the Lakefront Trail fronts Lake Michigan – and, for many visitors, walking along the shoreline is a highlight of a 3 Day Itinerary for Chicago.
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 Travel Plan is not complete without consuming at least one hot dog. Chicago Dogs are noted for being ‘dragged through the garden’. Meaning they’re piled high with mustard, onions, relish, tomatoes and a dill pickle spear sprinkled with celery salt (but never ketchup!).
Unarguably, the place to get a Chicago Dog is at Portillo’s. This 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 sandwich, then go to Al’s #1 Italian Beef – an iconic Chicago eatery chain that was established in 1938.
Join a Chicago Food and Drink Tour
While we have included some of the must-eat restaurants in our Chicago on a Weekend Itinerary, there is still more feasting to do!
Rather than choosing one place for lunch, taste-test your way through the city. Join an expert guide in the local foodie scene to discover favorite haunts and all the classic fare. Get the details!
Explore Navy Pier Chicago
Complete your vacation to Chicago with an afternoon at Navy Pier. Like Pier 39 in San Francisco, Navy Pier caters mostly to tourists, but a fun and enjoyable time is had by all!
Featuring a wide array of restaurants, souvenir shops and art exhibitions, Navy Pier is a must-see in Chicago…and a great 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. We understand, however, that you may have other specific interests. Therefore, we are sharing more activities that you may want to add to your weekend trip to Chicago.
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 is on the famed Magnificent Mile; 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 in Chicago.
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 venue to include on your Chicago trip itinerary!
Top Museums in Chicago to Visit
Art Institute of Chicago: The city’s most famous art museum, we suggest buying Skip-the-Line Tickets.
Museum of Science and Industry: This hands-on, family-friendly institution is a good spot to visit if you are planning a trip to Chicago with children.
Museum of Contemporary Art: The fun and modern MCA is a fantastic place to visit on a weekend getaway to Chicago for art lovers.
Shedd Aquarium: Whether you are planning a Chicago trip with family, as a couple or with a group of friends, the state-of-the-art Shedd is a good addition to your Chicago vacation planner.
The Field Museum: A fascinating collection of mummies and dinosaurs, it’s an excellent stop on a 3 day trip to Chicago for natural history.
Adler Planetarium: If time permits, plan a day in Chicago that includes stargazing at the Adler Planetarium.
Pro Tip: Save money and skip lines with a Chicago CityPass!
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 enclaves – but by no means covered them all.
Some of the other fun places to explore in Chicago are Chinatown, Little Italy, Lincoln Park, Wicker Park, Boystown and Roscoe Village.
Tips For Planning Your Trip to Chicago
Now that you know what to do in Chicago in 3 days, we have some essential advice for your visit.
Organize your Chicago Travel Plan
There is a lot more to Chicago trip planning than determining what to see and do. Next we share our top tips for planning a vacation in Chicago.
As you research Chicago vacation ideas and start making reservations, organization is key. Our Printable Travel Planner will help keep track of all the details of your perfect Chicago travel itinerary!
How To Plan Chicago Trip Budget
A trip to Chicago can be expensive – but it doesn’t have to be. Travelers who are planning to spend a weekend in Chicago on a budget have many options for exciting entertainment.
We suggest skipping high-priced sights and partaking in many of the cheap and free things to do in Chicago. Get all our tips on how to plan frugal getaways for your budget Chicago trip!
How To Get to Chicago
An essential consideration for your Chicago trip itinerary is how to get there! The Windy City can be reached by car, bus, train or plane.
Flying To Chicago
There are two major Chicago airports: O’Hare International (ORD) and Midway (MDW). Both have their pros and cons.
O’Hare is an enormous airport with flights from around the world, but is far from the city center. Midway, much closer to downtown Chicago, is dominated by Southwest Airlines and they serve mostly US domestic destinations.
Both airports are connected via public transport (the Blue Line from ORD and the Orange Line from MDW), but visitors can also use Uber or private transport.
Start your search on SkyScanner – but first read our Top Tips for Finding Cheap Flights.
Chicago by Train
If you are traveling to Chicago from another city that is serviced by Amtrak, then you can also plan a Chicago 3 Days Itinerary by train. That said, the journey will likely take longer and could even be more expensive than flying!
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 can use the ‘L’ train, CTA buses, bikes and scooters along with ride shares.
Public Transportation
Chicago has one of the most extensive public transportation systems in America and makes getting around fairly easy.
The affordable fares can be paid using a Ventra account – and both 1-Day and 3-Day flat rate tickets are available. Find complete Chicago Transit fare info on the official site.
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.
Where To Stay in Chicago
Although there are thousands of options to choose from, for your Chicago vacation itinerary, we recommend choosing downtown accommodations.
Chicago Hotels
If you are going to splurge for 3 nights in Chicago, there is no better place than The Palmer House Hilton.
The historic property, 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 amenities that are most important to you and the map to find a prime location. Be sure to also read all of our Tips for Booking Hotels!
3 Day Trip Chicago Vacation Rentals
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 cancelation policy and extra fees before confirming your place.
What To Pack For Your Chicago Trip
We have a few final packing hacks for your 3 perfect days in Chicago. To start off, grab your FREE Packing Checklist!
Weather Appropriate Clothing
What you put in your suitcase or backpack will depend on the season. Winters can be frigidly cold, summers are often unbearably humid, springtime is wet and autumn can be any or all of those!
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 and all your other everyday travel essentials.
Durable Shoes
Our Chicago 3-Day Trip Itinerary includes a ton of walking. We recommend wearing comfortable shoes for trekking around the city. I like these lightweight trainers by New Balance and Kris prefers wearing Merrell trail shoes for city jaunts.
Travel Camera
Chicago is incredibly photogenic – so you will likely be snapping a lot of pictures! Instead of relying on your phone to capture the sights, we suggest upgrading to a real camera. We travel with a DSLR Canon Rebel and use a 18-135mm lens.
Start planning your trip in the US! Search for the lowest airfares, the best accommodations and fun things to do…then start packing! Want more advice? Head over to our Travel Planning Page for tips on traveling – and for country-specific information, take a look at our Travel Guides Page!
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