3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary

Chicago is a vibrant city that feels very alive, and with the perfect 3 days in Chicago itinerary, it’s possible to sample the best of the city over a long weekend!

The city is always on the move, and there isn’t an hour in the day that you won’t find at least 10 unique and adventurous things going on around town.

Music and food festivals pull out all the stops in Chicago, on top of the arts and cultural events that dot the city throughout the year.

Are you into food and drinks, lake views, and most of all, fun? Then Chicago is the place to be. There is enough here to explore for months, and we are going to pack all of the best events and activities into a 3 day long weekend itinerary to experience the essence of Chicago. 

Note: this Chicago blog post was written for Our Escape Clause by former Chicago locals Zach & Julie Ruhl, the travel couple behind Ruhls of the Road. Thanks for joining us, guys!

Day 1 in Chicago Itinerary: The Bean, Skydeck & Great Chicago Food

Chicago is an enormous place. The city covers miles in each direction, with awesome things to do located all over the map. Therefore, this Chicago itinerary is going to thoughtfully take you from place to place, minimizing travel time and maximizing adventure.

Your first day in any new city should no doubt include some of the most signature sightseeing highlights there–and this Chicago itinerary is no exception, starting with a popular activity that is relatively new in Chicago: the Riverwalk. The current version of the Riverwalk was completed in 2017 and is an excellent place to start your Chicago weekend getaway.

Start your weekend in Chicago with a walk on the Chicago Riverwalk.

The Chicago Riverwalk starts at Wolf Point, near where the Chicago River turns from East/West to North/South. From there, the Riverwalk continues for over a mile, to the point where the Chicago River meets Lake Michigan.

Along this beautiful walk, you’ll pass a few awesome cafes and restaurants. This is a great place for a morning coffee, watching the morning hustle and bustle of America’s third-largest city. On top of that, the morning walk counts as your exercise for the day!

If you fall in love with the Riverwalk, then come back for a happy hour one evening. Riverside wineries and bars open up during the evening, complete with sets of outdoor games, live music, and some great entertainment! 

Check out Millennium Park.

At the end of the Chicago Riverwalk, you’ll reach Lake Michigan. Turn right here and head South to Millenium Park, where you’ll find an excellent location for soaking in the Chicago skyline from a beautiful park in the huge city center.

Millennium Park is an awesome Chicago sightseeing destination for two reasons. First off, it is just a great park full of fun things to do in Chicago!

There is an awesome playground for kids to play on, a great dog park for your four-legged friends, a huge green space to sprawl out for a picnic, a live music amphitheater, the Crown Fountain with a reflecting pool, endless gardens, and so much more!

You could spend a whole day at Millenium Park and not grow bored.

The second reason Millenium Park is so great is its proximity to everything. The park is great, but what makes it so impressive is that you are literally in a natural oasis amidst the concrete jungle of downtown Chicago.

Look around you while in the park, and you’ll see the towering structures of the Willis Tower, the Aon Center, and the rest of the enormous Chicago skyline.

Snap photos at The Bean.

At the edge of Millenium Park is The Bean, AKA Cloud Gate, Chicago’s most photographed (unofficial) monument.

The Bean is a huge monument, standing over 30 feet tall and 60 feet long, that is made of polished chrome and has no visible seams. This structure is truly unique and is an awesome downtown Chicago sight. 

The Bean is perfectly reflective, and due to its shape, the reflections can make for very fun images. It is essentially a gigantic magic mirror, placed in the middle of a bustling downtown environment.

Spend some time enjoying the fun reflections you can see as you walk in a circle around and under The Bean, then head for some food.

Downtown Chicago should have plenty of options on your way to your next stop: the Willis Tower. 

Admire views of Chicago from the Willis Tower Skydeck.

The Willis Tower is Chicago’s tallest building and the second tallest in the United States. At one point, this skyscraper was even the tallest building in the whole world, and held that title for 25 years! There’s no doubt that this is a must-see spot on any 3 day Chicago itinerary.

When you visit the Willis Tower, there are really two things you need to do. First off, admire the size of this monstrosity from below. The building literally reaches into the sky, and from the bottom seems impossibly huge. Walk around it marveling upwards, just make sure to lose your attention and wander into the city streets!

The other way to see the Willis Tower is, of course, from the top. The Skydeck is at the very top of the building, where you can see Chicago stretch beneath you for miles and miles in each direction into the horizon.

If you have the stomach for it, there is even a glass-bottomed section where you can literally step out into the sky, or at least it looks that way. From the glass floor, you can see down over 1,000 feet to the streets beneath you. This is quite an incredible experience and one that you won’t get anywhere else in the United States!

Book your Skydeck tickets for the Willis Tower today!

Finish your first day in Chicago in West Loop on Randolph.

The West Loop is an up-and-coming neighborhood in Chicago. This area seemingly has a great new restaurant pop up each week and has some of the most delicious food and one of the most fun atmospheres in the city.

Randolph Street in the West Loop is the culinary center of the neighborhood and is where you should head for dinner and drinks on your first day in Chicago. If you have the time and energy, the very best activity is to have a drink at a few different places, hopping from place to place and soaking up as much of this wonderful neighborhood as you can.

Each restaurant will have a unique vibe and atmosphere, so keep hopping around until you find the one you love best.

Want to make sure you experience the best food in the neighborhood?

Add this popular West Loop Food Tourto your Chicago itinerary!

Close out your first night in Chicago at an Irish pub.

Chicago has a huge Irish population, and therefore quite a few Irish pubs located around the city. Our best recommendation is to find one close to your hotel and pop in for a Guinness as a night-cap. Enjoy the Chicago atmosphere, and then head to your hotel to get some sleep before heading off on your second day’s worth of fun things to do in Chicago!

Day 2 in Chicago Itinerary: Lincoln Park, Wrigley Field & Beyond

Day 2 in Chicago is going to be a day full of exploring Chicago’s famous North Side. The North Side is awash with classic Chicago food options (Chicago loves its food…) as well as awesome sites to see and things to do. First up is the famous Lincoln Park.

Start the day with a stroll through Lincoln Park.

Lincoln Park is a huge and sprawling greenspace alongside Lake Michigan for 7 long miles. This is, in fact, the largest park in all of Chicago! And it also may very well be the most beautiful.

Alongside Lake Michigan, Lincoln Park has a few different beaches, as well as seemingly endless biking and walking trails. If you would rather bike than walk, then there are many bike rental options scattered all around the park, and around Chicago as a whole.

While strolling or biking through Lincoln Park, make sure to stop and see the Belmont Rocks, North Pond, and the Signal of Peace Monument. Along the way, admire the natural beauty and enjoy the sounds of birds singing as you bring on your second day in Chicago.

Soak up the sun at North Avenue Beach.

North Avenue Beach is one of Chicago’s largest and most popular beaches. Located right alongside Lake Michigan, this vast expanse of white sand makes for a great place to enjoy the beautiful Chicago summer sun.

If you are traveling with a group, then there are opportunities for some beach volleyball at North Avenue Beach! At the beach, you can rent a net and a ball (rentals are by the hour) and play some volleyball on the sand in view of the Chicago skyline!

While at North Avenue Beach, you must make a stop at the famous beach house that is shaped like a boat. This is also the location of Castaways, a bar and grill on the roof of the beach house serving yummy drinks with an incredible view. 

Head to Wrigley Field & Wrigleyville.

You can’t visit the North Side of Chicago and not see Wrigley Field. As one of the most famous baseball stadiums in existence, and the home of the Chicago Cubs, this is a must-see stadium, especially for sports fans.

Wrigley Field is located right in the heart of Wrigleyville on the North Side. Surrounded by residential areas and a huge bar and restaurant scene, this area is a magnet for good times, especially when the hometown Cubs are lacing up their cleats for a game.

If you are fortunate enough to be in Chicago while the Cubs are playing, head to Wrigley just for the experience of people watching and cheering on the hometown team. If you’d like, you could even try and buy some tickets, and usually, you can get a good deal on seats if you are okay purchasing them after the game is already in the 2nd or 3rd inning.

Wrigleyville, the neighborhood surrounding Wrigley Field, is an excellent place to hang out, have a drink, and hop around a few of the local establishments. Each of them has a great atmosphere, delicious, food, and of course a wide array of beers on tap.

Sample some Malort.

Malort is a Chicago specialty liquor and is something anyone over 21 should try when they visit the Windy City.

The liquor itself is not good because of taste, in fact, it tastes pretty bitter, and most people find it awful. However, it is all about the experience of trying something the locals love! If you’d like to experience the local culture of Chicago, then you have to try Malort at least once.

Finish the Day at the John Hancock Center Signature Lounge.

The John Hancock Center is the best building in Chicago. That may be a controversial opinion, but it is so true. The enormous slanted walls of the Hancock reach over 1,000 feet into the Chicago sky, with huge beams in a crisscrossing X pattern the entire way up. The building is an architectural masterpiece and is a wonder to see from the base.

The best place to experience the Hancock Center, however, is not from the base. It is from the Signature Room.

What is the Signature Room? It is an incredible 95th-floor bar and restaurant with an absolutely stunning view of Chicago. The Signature Room offers a 360-degree view of Chicago from above and is especially breathtaking as the sun sets and the sea of lights emerges beneath you.

Experiencing an evening at the Signature Room is a wonderful experience, and will be a highlight of your visit to Chicago. If you are visiting on a budget, just order a drink here, as dinner can be expensive!

Day 3 in Chicago Itinerary: Magnificent Mile, Navy Pier & An Afternoon Adventure

Day 3 is going to be spent exploring more awesome sites and destinations in downtown Chicago. It is going to be a day where you can see as much as you want, and take it all in at your own pace. Choose your own adventure and make today special as you finish up your long weekend in Chicago!

Walk down the Magnificent Mile.

Start the day with a trip down the Magnificent Mile. This is a section of Michigan Avenue that is the retail center of Chicago. The street is lined on both sides with tons and tons of flagship stores, boutiques, and shopping malls.

Along the Magnificent Mile, in addition to all of the premier shopping, there are a few awesome sights you’ll see during this part of your Chicago weekend getaway.

The Wrigley Building is an awesome structure located right where Michigan Avenue meets the Chicago River. The Tribune Tower and the Chicago Water Tower are also wonderful landmarks along this stretch.

Explore Navy Pier.

Just a few blocks from the Magnificent Mile is Navy Pier, an absolute must-visit destination on any Chicago visit. The Navy Pier is, as the name suggests, a large pier, formerly used by the Navy, that extends straight out into Lake Michigan. 

These days, Navy Pier is an awesome destination that is used for a wide variety of attractions. First off, there is almost always some form of live entertainment or shows that are happening over a weekend at Navy Pier. On top of that, the pier is lined with awesome bars and restaurants, as well as shops and boutiques.

The view from the end of Navy Pier is excellent. First off, you’ll get to see the vast expanse of Lake Michigan on 3 sides of the pier. However, when you look back at the city, you’ll get a view of the full skyline including the Willis Tower and the Hancock Center. Do you want an even better view? Because there is one way to get it… There is a HUGE Ferris wheel that you can ride to get a stupendous view of the entire Chicago skyline and Lake Michigan!

Visit Buckingham Fountain in Grant Park.

After exploring Navy Pier, head to Grant Park, another of Chicago’s excellent downtown parks. Here you’ll have the chance to explore a huge area of green space, complete with monuments, statues, and a great lakeside walkway. At the heart of Grant Park, you’ll see Chicago’s most famous and beautiful fountain: Buckingham Fountain

Buckingham Fountain is at the center of Grant Park and is a great place to sit and enjoy a coffee or picnic. The fountain itself is beautiful, but it is made even better by the great Chicago skyline in front of you, and Lake Michigan behind.

Further South in Grant Park you’ll find three other excellent Chicago sightseeing spots to consider adding to your 3 day Chicago itinerary:

Field Museum, Shedd Aquarium + Adler Planetarium

On the south side of Grant Park are 3 beautiful buildings, each of which houses an awesome adventure. The Field Museum is one of the largest natural history museums in the world and is home to some of the best exhibits you can possibly imagine. When we visited in the past, the dinosaur exhibit left us astounded, as they had a full-size Tyrannosaurus Rex named Sue!

The Shedd Aquarium is a world-class aquarium located just east of the Field Museum on Lake Michigan. This aquarium is stunning both from the outside and inside and offers hours of exploration as you make your way through the grounds.

Finally, the Adler Planetarium, America’s FIRST planetarium, is a wonderful place. This place offers the chance to explore things that are out of this world, literally. If you are at all interested in space, astronomy, or astrophysics, then you will have the time of your life at the Adler Planetarium.

Finish your long weekend in Chicago at River North.

River North is the area just north of the Chicago River. Whoever named it wasn’t very creative, but they were very accurate.

River North is absolutely FULL of awesome bar and restaurant destinations. As with many neighborhoods in Chicago, the best way to experience it is by hopping from place to place. When you find a place you love, stay as long as you’d like, then move along to the next place! That is the Chicago way of experiencing the nightlife.

Where to Stay for 3 Days in Chicago

Chicago is an enormous place, sprawling for miles and miles. The downtown area has many neighborhoods, each of which has pros and cons for visitors to the Windy City.

The best places to stay for 3 days in Chicago are near the Chicago River, specifically River North, Gold Coast, Streeterville, and The Loop.

In addition to those, a few more great neighborhoods are Lakeview, Lincoln Park, West Loop (which is home to great Chicago street art), Near North, and Old Town.

Here are a few great hotel recommendations for budget, mid-range, and luxury travelers.

Budget

Godfrey Hotel — The Godfrey Hotel is in the River North neighborhood, and is right in the middle of many of the best activities on your 3 day Chicago itinerary. On top of the great location, the hotel is beautiful on the inside and gets excellent reviews. The Godfrey Hotel is a wonderful place to hang your hat while exploring Chicago.

Check rates & book your stay at The Godfrey Hotel today!

Mid-range

Hyatt Regency Chicago — The Hyatt Regency Chicago is located in The Loop neighborhood, right on the Chicago River.

Many of the rooms in the Hyatt Regency have beautiful views of the Chicago River, the skyline, and the city streets.

The rooms are wonderful, the price is good, and the location is excellent. Additionally, the fitness center, meeting rooms, an on-site bar and restaurant, and access to Chicago activities make the Hyatt Regency one of the best places to stay in Chicago.

Check rates & book your stay at the Hyatt Regency Chicago today!

Luxury

The Langham — Now, to the creme de la creme. If you’re a luxury traveler looking for the best hotel in Chicago, look no further than The Langham.

First off, the location could not be better. Located right on the Chicago River in River North, you’ll be within walking distance of nearly everything on your itinerary.

Additionally, The Langham pulls out all the stops when it comes to amenities. The on-site spa, fitness center, pool, and deluxe bar and restaurant are all five stars. Of course, the rooms are wonderful as well, and nearly all have stunning views of the cityscape.

Check rates & book your stay at The Langham today!

Where to Eat During Your Chicago Weekend Getaway

Chicago and food go hand in hand. You could explore a new food destination in Chicago every night for the rest of your life, and not eat at the same place twice. Not going to fact check that, but it is probably true. There are awesome restaurants on every corner, all across the city!

Here are four must-visit restaurants in Chicago that we love. 

Chicago-Style Pizza – Giordano’s

You can’t come to Chicago and not try some Chicago-style pizza. You literally can’t, it is impossible. The best Chicago-style pizza is at Giordano’s. The pizza here is absolutely LOADED with cheese and toppings, more than you have ever had, guaranteed. One slice and you’ll be satisfied, two slices and you’ll be stuffed. Be prepared to have leftovers!

Portillo’s

Portillo’s is a Chicago institution. This started as The Dog House, a hot dog stand, and grew into Portillo’s, a delicious restaurant serving beef, burgers, and Chicago-style hot dogs all across the city. Portillo’s is yummy, quick, and is a Chicago must. Try the chocolate cake shake, you’ll be glad you did.

Happy Camper

Happy Camper is an excellent classic pizza place located in the Near North neighborhood, which offers an excellent atmosphere. This is a great place to watch sports, meet friends, enjoy a happy hour, and of course, try some pizza!

The toppings are creative at Happy Camper, and the pizza is DELICIOUS. There is also a huge selection of local and imported beers to try.

Girl and the Goat

Girl and the Goat is an absolutely EXCELLENT restaurant located in the West Loop neighborhood on Randolph Street. The food here is delicious and is very creatively and expertly prepared.

Call ahead for a reservation at Girl and the Goat, as there may be a long wait if you just show up asking for a table. If you do just show up, however, this is worth the wait.

And you can walk across the street to one of the many bars on Randolph while you wait for a table at Girl and the Goat!

Bonus: take a Chicago food tour!

In a city as centered around food as Chicago, taking a food tour is one of the best ways to explore the city’s cuisine. 

Not only will you be able to sample a wide variety of classic dishes without committing to a whole portion, you’ll also learn plenty about Chicago’s history and culture along the way!

This popular food tour gets rave reviews and is an excellent addition to your long weekend in Chicago.

Book your food tour in Chicago today!

Getting Around During 3 Days in Chicago

Getting around for 3 days in Chicago is in most ways easy, but can sometimes be challenging.

The public transport system is the easiest and most inexpensive way to get around, followed by cabs/Uber/Lyft, and finally driving yourself.

Much of the 3 days in Chicago itinerary laid out above, however, can all be completed by exploring on foot, especially from the recommended hotels. The awesome destinations and great parks are relatively close together and can be reached with a nice walk in the Chicago air.

Chicago has one of the best public transport systems in the US. The elevated train, AKA the ‘L’, brings people across Chicago east, west, north, and south. The ‘L’ stops at all of the amazing sites in the city, as well as O’Hare Airport, Midway Airport, and all the major thoroughfares.

If you would rather avoid public transportation, then the best way to travel around during this 3 day Chicago itinerary is with a cab/Uber/Lyft. Traveling this way is likely the fastest if you can avoid rush hour, and the most convenient. However, it will be more expensive than using the ‘L’ trains.

Finally, you, of course, have the option of driving yourself around town. In our opinion, this is the most stressful way to get around, as you’ll have to worry about parking in the busy downtown streets. This is a challenge and is made worse considering that many hotels offer parking fees.

When to Spend a Long Weekend in Chicago

The best time to plan a long weekend in Chicago is during the summer. The weather during the summer is absolutely perfect, and it’s definitely the easiest time to pack light for a Chicago vacation (if you visit during the blustery winter, be sure to carefully consider what to wear in Chicago!). This is also the best time to explore the awesome parks, beaches, and outdoor destinations in the Windy City.

Each year in the summer, Lollapalooza brings huge crowds looking for an awesome time and great music. Lollapalooza draws many of the best music acts in the world, so traveling to Chicago during the music festival is a great opportunity. On top of this festival, many great music artists perform regularly at Wrigley Field, Soldier Field, the United Center, and the other great venues across Chicago.

Coming in a close second to the Chicago summer is the spring when the city defrosts after its long Chicago winter and comes alive. There is nothing quite like spending 3 days in Chicago when the atmosphere is on the rise, as it is in spring.

Also during this time is St. Patrick’s Day, one of the largest holidays in Chicago. On St. Patrick’s Day the river is dyed bright green, and the partygoers are out in force.

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