Chicago itinerary 4 days




















When it comes to wining and dining, the world really is your oyster in the Loop. After such a big day, you may want to call it a somewhat early night. Of course, if you want to go out and rage, go for it! This is the perfect spot to load up with a big breakfast and coffee before another big day in the city. After breakfast, walk across the street to check out Agora — a sculpture composed of headless figures.

Keep walking east towards the lake to reach the Museum Campus. To be honest, the aquarium is pretty sweet. There are a few cafes and food stands around the museum campus, so go ahead and grab a snack and a drink before powering on.

The museum campus is the southern part of Grant Park. There are plenty of benches if you need to sit down and chill for a bit. Grant Park also hosts some of the biggest events in the city, such as the Taste of Chicago and Lollapalooza. Hug the coast and keep walking north along the lake until you reach the Riverwalk. This scenic pedestrian path along the Chicago River is the perfect place for a leisurely stroll.

If your feet are feeling a bit tired from all the walking, you can enjoy the spectacular Chicago architecture on this fantastic river cruise instead. Taking in the sights along the Chicago River is definitely one of the top things to do in Chicago in 3 days. Wendella Boats has an architecture river cruise that comes highly recommended. The latter is home to the City Gallery, which has Chicago-focused photography exhibits.

Of course, you can add whatever other toppings you like as well. This pizza is seriously delicious and filling, so I wanted to make sure you could at least have a few slices. There are plenty of places cooking up Chicago-style pizza, but I brought you here because two of the best are easily accessible. Get to the corner of Michigan and Superior and you have an important choice to make.

Just go ahead and flip a coin because you win either way. First up, you can take a ride on the Centennial Ferris Wheel. From the end of May until the end of August, Navy Pier also hosts bi-weekly fireworks shows.

These happen on Wednesdays at PM and Saturdays at To take in the spectacle, you can find a spot to stand on the Navy Pier or sign up for an evening cruise. Enjoying the fireworks as you cruise around is a great addition to your Chicago itinerary. If you have any gas left in the tank after all of the activities at the Navy Pier, congratulations!

I just ran you ragged all over Chicago on day two. For many, that will probably involve grabbing a casual drink from the hotel bar and getting some sleep. Go for it, you crazy kids! Your options are endless. This awesome tiki bar has an impressive selection of cocktails that will transport you to the Caribbean in no time. Bars in Chicago typically close at 2 AM, but there are several that stay open as late as 4 on the weekend.

How early the last day of your Chicago itinerary starts depends entirely on how late your night went! Those who already regret ordering that last round may need to sleep in a bit and smash a greasy brunch, while the go-getter set who actually slept will be up and at them. Life is all about choices, people! Whatever you did the night before, get some food and caffeine in your system and get out there to wind down 3 perfect days in Chicago.

Our third and final day in Chicago starts off with a leisurely museum visit. Within a few blocks of each other, you can take your pick between three excellent museums. Those more interested in architecture and antiques may want to hit the Richard H. Driehaus Museum. Chicago is very much a sports city, as people here are very passionate about their teams. Check out the Chicago Sports Museum, which is full of memorabilia and plenty of fun exhibits. This observation deck on the 94th floor of the John Hancock Building provides a whole different perspective on the city that you will definitely want to see.

If you need some hair of the dog instead, you can grab a ticket that includes your choice of adult beverage. Sunday Funday! From the Navy Pier, you can catch numerous different types of cruises to suit your interests, like a dinner cruise, buffet cruise, or sport-themed cruise. You can also choose between different types of boats! Our favorite option is an architectural river tour, because it allows you to learn so much about the buildings you pass, both world-famous and hidden gems.

Relax and enjoy a drink from the bar. Chicago is known as the birthplace of the skyscraper, and the home of modern American architecture. There is so much to learn and appreciate here.

Skip the ticket office and proceed directly to boarding by pre-purchasing your ticket online. This foodie Chicago walking tour is a simple classic — stroll through the city learning more about it from a local, while trying all of its best and most exciting foods. Your guide is knowledgeable and friendly, and will tell you about much more than just the food!

The city has so much to see and explore and has such an interesting history, including famous s gangsters like Al Capone. Chicago is famous for its American-style food innovations, like the deep-dish style pizza, and Chicago-style hot dogs.

The tour lasts three-hours long, so you have ample time to eat and explore. You will also get to meet new people on your tour, and enjoy your meals with new friends, laughing and chatting. The museum was once the mansion of Samuel Nickerson and his family, a local banker. Now, after two restorations over the years, it explores the art, design, and architecture of that period to the present.

The permanent collection of period decorative arts suits their surroundings perfectly. Educational and cultural programs contribute to exhibitions which contextualize the Gilded Age and illuminate the vibrant history and culture Chicago. Enjoy all the little details that make this museum stand out among much larger ones in the country.

Each detail is unique, many inspired by locations around the world, others by jazz, music, and the urban culture of Chicago. Year round the museum features rotating exhibits of modern and contemporary art, which contrasts with the location in interesting and beautiful ways. Spend a few hours here- the more you look, the more you will see. The staff is also very passionate about their work, and the guides are knowledgeable.

In fact, we certainly recommend the guided tour. You will want to learn more about it! The Museum is located just steps from the Magnificent Mile, and is easy to find! An alternative way of experiencing Chicago is the Mob and Crime bus tour. See famous Chicago crime scenes from the 19th century through to modern times. Visit the historical criminal courthouse, an architectural landmark where some of the biggest cases were tried.

Stake out other landmarks and learn about the darker, more criminal side of their history. For a time, gangsters ran Chicago. You will also have the opportunity to leave the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. On the third day of your itinerary in Chicago, go watch a football game! Most games are of course played on weekends. The team and the stadium have a rich history and a loyal following.

Just enjoy the action and the great vibe! Soldier Field is an iconic football stadium, easy to get around and has lovely, efficient staff. Interestingly, it is still the third-smallest stadium in the NFL.

It looks exactly like a normal belt except for a SECRET interior pocket perfectly designed to hide a wad of cash or a passport copy. Never get caught with your pants down again! Unless you want to.

So how safe is Chicago? There are, however, some neighborhoods that are better to avoid. In these areas, gang violence and other criminal activities occur. Pickpockets are reasonably common in very busy areas, and we suggest you keep your belongings firmly by your side. Muggings also occur, particularly at night. These can be avoided by staying on well-lit, well-populated streets and avoiding dark or dingy areas.

Neighborhoods to avoid, particularly at night, are the far West Side of Chicago, which has very few tourist attractions and the Fuller Park area. Parts of Downtown Chicago get empty at night, and therefore risky. North Side remains safe throughout the night, and you can walk comfortably here as long as you take the common-sense safety precautions. Natural hazards do occur occasionally, but their safety risk tends to be low.

There is, however, a higher risk during winter. And have you thought about getting Travel Insurance for your trip? Chicago is near to four different states! You can get to other great cities easily and explore the beautiful surrounding area on these day trips from Chicago. The best of the day trips from Chicago has to be New York by air! The tour is very laid-back, with time to take in a show, do some shopping, or set out on a little extra sightseeing!

The tour includes a round trip from Chicago, a two-course lunch in Times Square, and your sightseeing bus trip. So different to Chicago and yet so close. Enjoy wine tastings at each of them and a gourmet lunch. Have a delicious meal overlooking a vineyard and enjoy some time walking through and learning about the farms. The tour includes tastings, lunch, bottled waters, and a departure toast to start things off right!

Get to know the people on your tour and enjoy leaving the city behind for a day. This half-day tour of the city is one for the books! Travel through the north and south financial districts, admiring iconic buildings and sculptures. You will also look out from the top of the John Hancock Building, and try to identify all four states! The tour is a great activity to bring friends who only have one day in Chicago. If you fancy enjoying the windy cities magnificent skyline with a cold alcoholic drink, then try to find one of Chicagos rooftop bars — but drink responsibly!

Fly to Detroit, where you can explore the very different American city with a walking tour before setting out on your own. The tour is a great introduction to the city.

Chat with fellow tourists and a knowledgeable local. Catch a short flight to Milwaukee, where you can join an exciting and fun scavenger hunt adventure! You can stop and go as you please, and take as much time as you need, admiring and learning about the attractions as you go along. You use your smartphone to play the game and navigate the historic streets of Milwaukee, enjoying its modern and unique culture.

With so many world-class museums, sports centers, places of culture, music, food and fun, Chicago is one of the best cities in the world. You can explore the history of the city, and the natural history of the world!

Chicago brings together elements of our whole world in ways unique to the vibrant city. With our Chicago itinerary, you will certainly never have a dull moment. Pack walking shoes, an umbrella, and be sure to bring your camera. You will want to capture the immense skyscrapers as well as the little details that make Chicago iconic! Find out how YOU can support the site.

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The aquarium was separated into sections, each section featuring a different part of the world. The fish in each section were the fish that could be found in that part of the world.

The aquarium has several educational shows throughout the day as well, where you can learn about various animals such as dolphins, sea lions, penguins, and more while watching them do cool tricks. My boyfriend and I easily spent three hours at the Shedd aquarium.

However, if you plan on visiting the aquarium with little ones, I suggest planning on spending a majority of the day there. Personally, I liked the views from Chicago better, but I thought the Ledge was a cooler experience. If you have to choose, you can check out this comparison between Skydeck Chicago and Chicago. Probably the most iconic part of Navy Pier is the Centennial Wheel, a large ferris wheel. Towards the end of the pier, you can also get a really good view of the city.

It also holds several free events from time to time, so make sure to check the calendar before you go. The gardens is entirely inside, so even if you go to Chicago in the winter, you can enjoy the gardens.

Chicago has a relatively extensive public transit system called the Chicago Transit Authority or CTA, and is probably the cheapest way to get around the city. If you decide to use the public transit system for a majority of your trip, I recommend picking up a Chicago Ventra Card.

It is a reloadable charge card that you can use for riding the bus, train, and subway. You can purchase these online in advance from their website or buy one from one of their retailers.

You can also use the Plan A Trip section of their website to figure out the best bus or rail line to get you where you need to go. My boyfriend and I chose to stay at Best Western River North Hotel because we felt like it was a good middle of the road option. However, because we were limited on time, we wanted to stay in or close to downtown for easy access to all our destinations.

The other thing we had to keep in the back of our mind was parking rates since we drove to Chicago. Wondering what to bring on your trip? The answer to that question will likely depend on when you go since Chicago experiences all four seasons. For most of my long weekend in Chicago, I wore a winter coat , winter hat , gloves , a thick scarf , and winter boots.

I also typically wore a a long sleeve shirt and heavy sweater underneath my coat as well as leggings underneath my jeans. On the other hand, my boyfriend walked around most of the weekend in just a long sleeve shirt, sweater, scarf, and jeans.



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