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(There are also tours of the stadium offered during the off season). Wendella Boats has an architecture river cruise that comes highly recommended. Make sure you have your camera for this one, as you’ll get some epic views of the city. Since you only have 3 days in Chicago, there are many things you will want to pack into your itinerary. Try to include a little bit of everything when you plan your 3-day schedule. Remember, if you are visiting over a long weekend, things will be packed with locals and tourists.
River Cruise
This allows you to bypass the general admission line at entrances AND offers expedited access to ticketed special exhibitions. Having the Chicago CityPASS can save you a lot of time when sightseeing. When I was visiting Chicago in the summer, there was a huge line up to get into the Art Institute of Chicago.
Chicago Architectural River Cruise
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After exploring Wicker Park, take transit to the Gold Coast neighborhood which is nestled just north of downtown Chicago. MSI has over 400,000 square foot of exhibit space and is the largest science museum in the Western Hemisphere. Take transit (or walk) up Michigan Avenue north of the river to shop the Magnificent Mile. All-Access Admission is included when you purchase the Chicago CityPASS. Most visitors spend between 2 and 3.5 hours exploring the Shedd Aquarium.
Recommended Experiences in Chicago
You will see everything from the Museum Campus and Soldier Field to Navy Pier and the Centennial Wheel. Tickets for the Skydeck are included with a Go Chicago pass or you can get your tickets on the ground floor of the Willis Tower. This Ferris wheel is super-sized and is visible throughout the city. Book tickets in advance to make sure you get to ride the wheel. There are also a few other rides nearby that you may find to be wonderful fun. If you have a Go Chicago pass, tickets for the wheel are included.
It’s only 45 minutes long but will still show you the city’s most breathtaking landmarks. If you’ve only got 3 days in Chicago, then going on a river cruise has to be at the top of your list. Chicago River architecture cruises usually last around 1.5 hours and typically start at DuSable Bridge. Usually, you’d head to a Starbucks for a quick coffee but not here!
This is a great spot to unwind and take a break from all the hustle and bustle of the city. Trust me, if you’re into coffee then you don’t want to miss out on this place during your 3 day trip to Chicago. They have multiple locations throughout the city but this one is actually at Navy Pier so you won’t have to wander far. Below you can find a customized map that includes all the locations you’re going to visit on this Chicago itinerary. Hotel EMC2 is located in Streeterville and is right by the Magnificent Mile and Downtown Chicago.
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Great location just steps from Michigan Avenue and one block from Lake Michigan. For Chicago style hot dogs (remember, no ketchup allowed) try Portillos, a popular chain. Chicago has a long history of organized crime and is famous for being the home of mafia figure Al Capone. There are many mob tours for those that want to learn more about the history of organized crime.
In the middle is the Lincoln Park Zoo, which is totally free to visit. Sightseeing gets expensive, so this awesome free attraction is definitely one of the top things for any Chicago itinerary. On a beautiful day in Chicago, it’s hard to beat lounging on the beach and swimming in the lake. You can also play some beach volleyball and rent a SUP or bike if you want some more activity.
Shoreline Architecture River Tours
If you’re looking to do some shopping, you’ll find everything from high-end stores to budget-friendly options. And when you need a break from shopping, there are plenty of restaurants and cafes to choose from. Some of the most popular attractions include the John Hancock Center, the Wrigley Building, and the Tribune Tower.
If the weather is nice, grab lunch to-go and eat it in Grant Park (just above Museum Campus). This is a nice way to take a break, relax, and enjoy the scenery. This includes entry to all the permanent exhibits and regularly priced ticketed exhibitions, plus your choice of on digital 3D film. Here you can store your bags and other personal belongings if you want. It’s usually busy during the day, but you might get lucky by going early in the morning before other tourists arrive. There is also a great spot to eat at the Plaza at Park Grill here.
These fun experiences offer guests panoramic city views along with entertaining and enlightening commentary about Chicago’s architecture and history. In a perfect world, the Cubs would be playing a night game while you are visiting Chicago. You could head north to Wrigley Field and enjoy America’s pastime at the 2nd-oldest ballpark in the country.
You can also use the Curb app (for taxis) or ridesharing apps (Lyft and Uber) to get around Chicago. Chicago is an easy city to get around in with many public transportation options. Both Chicago airports – Chicago O’Hare (ORD) and Chicago Midway (MDW) – are connected to downtown Chicago by train.
This deep dish pizza is seriously delicious and filling, so I wanted to make sure you could at least have a few slices. Even if you visited on your walking tour, it’s worth it to double back to Millennium Park for further exploration. The best way to kick-off your Chicago itinerary is by taking a walking tour of the Loop. This area of downtown is where you’ll find a majority of the sights in Chitown. If you’re spending 3 days in Chicago, your best bet is to just pick up an unlimited CTA pass.
If you want to skip the long lines, consider getting Expedited Entry tickets. This will save you a ton of time with an express line to the elevators. Plan to spend at least one hour at the Skydeck (depending on how busy it is and how long you wish to stay).
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. Now you see why I’ve been torturing you by making you walk around all day waiting for dinner!
The menu is modern American and they have lots of amazing cocktails and drinks. Once you come down from 360 Chicago in John Hancock building, you have plenty of options for lunch. Within a few blocks, you can find Cuban, Vietnamese, Mediterranean, and the Chicago staple of deep dish pizza. 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.
