Introduction: Discovering the Windy City:
Chicago is known for its beautiful skyline, unique architecture, and huge buildings bends with beautiful parks. When people think of The Windy City, it is usually about cold winters and painful wind chills, but the city of Chicago has so much to offer to its new travelers. You can’t visit Chicago without doing these, the Midwest’s largest city has the bean, the large and beautiful Lake Michigan. Chicago is the place for people who love the outdoors and want to spend time in some green spaces, Chicago is the perfect city to visit.
Chicago has some great activities to make your trip worthwhile. The Windy City has so much to offer, from attractions and places to see tied to the Great Chicago Fire to modern activities and great places to eat that make the city a thriving downtown hot spot. If you want to visit some of the fine dining establishments or want to eat some great food on a budget then don’t worry. The best places to eat brunch in the Blues clubs along with some of the best places to experience the great outdoors.
Planning Before You Go:
Buying Plane Tickets:
First thing I did to start my trip to Chicago was buy plane tickets. I can fly into either O’Hare International Airport (ORD) or Midway International Airport (MDW). But O’Hare International Airport is bigger and has more international flights, while Midway is smaller and has more domestic flights. You can choose based on budget and location.
Remember to buy tickets from Kayak as soon as possible, so you can get the best prices. Also, try to get tickets so that you have enough time to enjoy your trip.
Where to Stay:
In Chicago, You have a choice of where to stay, from a 5-star hotel to a 1-star someone can pick based on budget. The best areas to stay are The Loop, River North, and Magnificent Mile. These are located near most of the attractions of the city. If you are on a budget, Kayak options are also plentiful, especially in trendy neighborhoods like Wicker Park and Logan Square.
Travel Insurance:
Travel Insurance is a good thing to have with you in every trip. It is a safety net for trip cancellations, emergencies, and lost luggage. You can get financial protection from Travel Gaurd in the case of an emergency on your trip.
Packing Essentials:
Packing depends on the season you are coming. Summers are warm, while winters can be freezing. Here are some essential items to bring:
01. Weather appropriate clothing (jackets and sweaters for winter and light clothing for summer)
02. Comfortable shoes (you will be doing a lot of walking)
03. Chargers and power banks
04. Toiletries
05. Travel documents (ID, passport, boarding tickets)
2. Planning The Trip
How to get to the airport:
I planned how to get to the airport before my flight. If you are driving, taking a rideshare, or using public transport, make sure you leave enough time to avoid any stress.
Checking in:
It is a must to arrive to the airport 2 hours before your flight to check in and go through security. Don’t forget to keep your ID or passport and your boarding ticket handy.
Flying Overhead:
My favorite part of flying was to be all of the little things I did to make myself feel comfortable. This consists of a neck pillow, a comfy hoodie, some headphones, and of course the snack I brought for the flight. I like to do some in flight entertainment. I like to avoid all of the turbulence that is typically expected going to the windy city.
Walking in Chicago:
Once I land in Chicago, I had a wi-fi bug that I attach to my mac so I can do personal things while I wait. I was do things like make a plan for a month, and I did that while keeping track of my arrival at Midway. As soon as the plane lands, everyone got detrained, and I used the Transport to the city. I grabbed a shuttle to the ‘L’ train for city transport which I like. The shuttle to ‘L’ Train transport to downtown Chicago is free, and then up to the Grand stop which is free.
Getting to your Hotel:
Once I check-In to Chicago , I took the ‘L’ train, a shuttle, and then I availed a taxi or a ride sharing app to my hotel.
Things to Do in Chicago for Free:
1: Hop On Hop Off Bus City Tour
Hop On Hop Off Bus City Tour is a good way to get to see some of the key features of the city. The tour comes with a ticket to ride the bus and a peek at the Chicago River and the busy Michigan Avenue. The bus also offers the opportunity to get off and back on attractions to see a variety of sights at their own convenience. The ticket is good for two days and makes it possible to avoid taxis while still getting to Willis Tower and Navy Pier. The bus is a good way to see the most important sites while breathing the fresh air.
2: Shopping on Magnificent Mile
Mag Mile, or Michigan Avenue, is the best place to shop in Chicago. There are big name department stores like Nordstrom, and plenty of small cafe businesses to grab coffee and snacks. It’s the best place in the city to go for a nice walk, do some shopping, and check out the view of the Chicago River. There are a ton of different stores, so whether you are looking for some coffee or a new outfit, you’ll be able to find a place to buy gifts as well.
3: Stop by the Harry Potter Shop
If you’re a Harry Potter fan, the Harry Potter Shop in Chicago is a good place to check out. It’s right by Michigan Avenue and has a lot of merchandise. You can buy wands, Hogwarts school uniforms, and owl plushies. You can buy a drink called butter beer at the cafe, and you can feel like you’re in the Harry Potter world. It’s a great place to buy merchandise and take pictures with a model of the Hogwarts Express.
4: Enjoy Maggie Daley Park
Maggie Daley Park is located right next to Millennium Park, and is a great place to enjoy fun outdoor activities. Ice skating is available at the outdoor skating rink, and during summer, visitors can enjoy fun activities like mini golf. Kids can enjoy the Play Garden, a cool playground, and people of all ages can climb the rock wall. Whether you want to kick back and relax at the garden or you want to get active at the park, Maggie Daley Park is a great place to hang out with the family all day!
5: Listen to a Free Summer Concert
Millennium Park summer concerts are a great tradition in Chicago and a fantastic way for people to enjoy the Chicago summer. There are various concerts and music events at the Jay Pritzker Pavilion and the best part is, it is free from June until August. It’s a great place for music lovers to relax and listen to live music, and there are often amazing musicians and even rising stars. You and your friends can enjoy the great Chicago summer evening while watching a live concert.
6: Standing on The Ledge at Skydeck
If you have the guts to do it then Skydeck Chicago offers a one of a kind experience. The view from the 103rd floor Skydeck is one of a kind. The floor is made of glass which allows you to look straight down. You can also take an amazing picture above the clouds for a great social media experience. If you have the bravery to do it, stepping out on the ledge offers, you can enjoy one of the best views of the city sky. If you’d like to take the time to challenge your fear of heights, and enjoy the experience!
7: TILT at 360 Chicago
TILT at 360 Chicago offers another amazing experience filled with thrills. If you want to enjoy the Chicago skyline, the 94th floor is a great place to do it. If you want to step out and take an amazing picture, the view from the top of the overhang is incredible. You can take the view of the city from above and the experience is absolutely breathtaking. Afterwards, you can go to the Cloud Bar to get a drink and enjoy one of the best views of Chicago while you sip your cocktail.
8: Coffee with a View at Cloud Bar
Coffee at Cloud Bar on the 94th floor of 360 Chicago will surely be an interesting experience. You will be able to see the city and Lake Michigan while sipping your coffee. It really is a good place to relax and have a latte. You can enjoy a quiet moment when Cloud Bar is a good place to relax and have a latte. You can enjoy a quiet moment when sightseeing. Take a break at Cloud Bar’s and enjoy the amazing drinks and views.
9: Take a Helicopter Tour Over the City
Take a helicopter tour over the city and see it from a completely different view. FlyHeli is a good way to see the city from a different perspective. You can see the buildings over the Chicago River and the Chicago stadiums. This is a good chance to get pictures from the top of the city. You can spend the day in Chicago. If you are in town on July 4th, you can see the fireworks from the helicopter. You will never forget that experience.
Outdoor things to do in Chicago
10: Explore the American Girl Store
If you are planning a day trip with the family, stopping by the American Girl Store would be a fun option. The American Store offers an “experience” as opposed to just shopping which is located on the Mag Mile. The kids can get their dolls a hairdo at the doll salon while you shop for a new doll or accessories. You can top off the trip with a snack from the cafe, or a dessert for the kids.
11: Eat at Eataly
If you want to have a nice lunch, then head to Eataly. Eataly is an Italian market with different restaurants, selling everything from deep-dish pizza to homemade pasta which is located on Mag Mile. They also have Italian takeout, so you can get some to enjoy at home, along with a cookbook if you are into that kind of thing. Eataly is the place to go for Italian food if you are looking for either a casual lunch or a formal dining experience.
12: Go On an Architecture Cruise
The Chicago River hosts some great skyscrapers and even more Chicago architecture history. On an architecture cruise, you get some of the best sights and insights into the history of skyscrapers and other important infrastructure of Chicago. Besides the great skyscrapers that you will learn about, you will see the Wrigley Building, the Tribune Tower, and the Merchandise Mart. Enjoy the sights and the breeze as you learn about Chicago.
13: Snap a Picture at The Bean
Visit Cloud Gate (The Bean) in Millennium Park to get your Chicago photo. This famous stainless steel sculpture is a great place to take a funny photo. The reflective steel surface provides an incredible reflection of both the Chicago skyline and the people standing in front of it. It is a Chicago landmark that everyone must see.
Main Attractions in Chicago for Adults
Are you an adult or you want to enjoy Chicago and all that it has to offer? You are here for a wonderful surprise! No matter what your interests are, be it food, art, history, or even something that leans towards the adventurous, here are some things you most definitely have to do.
14: Walk Along the Chicago Riverwalk
The most picturesque of Chicago’s many beautiful locations and prominent sections of the Chicago River is the Riverwalk, a 2 km stretch walkway that is an ideal location to enjoy Chicago’s amazing skyline with all of its beautiful angled buildings and creative architectures, and want some refreshments? There are many restaurants, bars, and coffee shops offer a great variety of drinks and food.
It is a great location for simply spending time with friends and on the eating and drinking patio. Also, lots of excursion cruise ships offer chicago boat cruises and are available to rent for private parties. Also, perfect for a unique way of spending the day on the river. Chicago’s riverwalk is a great location for swim and paddle kayaks, and is often the best location for people to enjoy the river. However, there are various artistic and decorative public areas, installed stream green environment, and people watching (for the many joggers, runners, and people watching) of riverwalk is loved.
15: Visit The Bean
One of the most popular places to visit in Chicago is The Bean, or Cloud Gate, if you want to be formal about it. The Bean has been in Millennium Park since it was built. This stainless steel sculpture is 33 feet tall and weighs 110 tons. The best part about The Bean is that it makes for great photos as it reflects the city’s skyline. You can “Even walk under it and see the weird reflection of yourself. The Bean is great for a first time visit in Chicago.
16: Take a Boat Tour
A boat tour on the Chicago River is the best way to see the city’s history and tall buildings. The buildings along the river have a mixture of architectural styles such as Art Deco and Postmodernism. You may see and learn about the Willis Tower, which was previously known as the Sears Tower. You can visit several attractions for a small price, including the architectural boat tour with a CityPass,. This boat tour has a beautiful view of the Chicago skyline along the river, which is also the site of the Great Chicago Fire. This is a great option if you have a love for history.
17: The Ledge skydeck
The Ledge is at the Skydeck at Willis Tower on the 103rd floor. The Ledge has awesome height and wide view of the city with a 50 mile view. You can see four different states and the city below. It is a thrilling height experience.
18: Enjoy The Views from 360 Chicago
360 Chicago is a great place to enjoy amazing views of the city. It’s located on the 94th floor of the John Hancock building. Here, you can enjoy panoramic views of the city and Lake Michigan, making this a perfect place to enjoy the beauty of the city. There’s Tilt, which is a glass-panelled horizontal platform that tilts over the building for those looking for a thrill. You can go to the Cloud Bar and have a cocktail while you enjoy the views more calmly.
19: Check Out The Art Institute
The Art Institute of Chicago is the place to be for all the art lovers. It is especially known for being home to a breathtaking collection of Impressionist and Post-Impressionist paintings, including famous pieces by Monet, and Van Gogh. The museum has a lot of different activities and rotating exhibitions, so it is a fun place to go, whether you’re an art lover or just someone who wants to see some famous paintings. Don’t forget to book a private tour to fully enjoy the collection.
Top Things to do in Chicago this weekend:
20: Bikes, Bites, and Brews Tour – Chicago’s Exclusive Tour
The Bikes, Bites, and Brews Tour is made for people who like to bike, eat, and drink beer. On this tour, you will be guided to the trendy areas of Chicago, including Lincoln Park and the Lakefront Trail, where you will get to eat Chicago’s world famous Deep Dish Pizza and other city’s best eats like the Chicago hot dog and a chocolate brownie. In the 4.5 hours of this tour, you will eat and drink while enjoying other attractions of the city.
21: Enjoy a Day at Wrigley Field
Wrigley Field is a Chicago icon that all sports fans must visit. The Chicago Cubs play here, and it is one of the oldest baseball stadiums still in operation. Even if baseball isn’t your favorite sport, the lively environment of the Cubs games allows you to appreciate the passion many Chicagoans have for sport. The Cubs fans create a unique and lively experience for all visitors. If you plan to visit Chicago during the NFL season, you can also catch a basketball Soldiers Field Bears game.
22: Stroll the Magnificent Mile
Chicago’s top shopping and dining location is the Magnificent Mile. You can visit many high-end shops, trendy stores, and popular chain stores. If you want to take a break, there are also a lot of restaurants and coffee shops. If you want to be in a lively and exciting environment, you can visit all of the shops and restaurants. This is one of Chicago’s most popular areas.
23: Go To Free Concerts, Movies, or Yoga at Millenium Park
You can enjoy free concerts, movies, and yoga classes at Millenium Park. Yoga and Pilates classes are hosted in The Great Lawn and around The Bean which provide an opportunity to sit and engage with the community. A schedule of free yoga/pilates classes can be found on the Millenium Park website. If you enjoy working out, making art, or just relaxing, you should visit Millenium Park. There are various free activities offered at the park.
24: See Fireworks at Navy Pier
Navy Pier hosts free fireworks shows on Wednesdays and Saturdays at 9 pm. This attraction is located on the water, where you can also find a Ferris Wheel and a bunch of other rides. This fireworks show is a great way to end a long day of fun in Chicago, whether you are with friends or family. The FlyOver and simulator are fun to do before or after the fireworks show.
25: Kayaking on the Chicago River
If you want some more fun, why not consider kayaking on the Chicago River. There are both single and tandem kayaks available. It’s a fun way to see the city from the water and get a different view of Chicago’s amazing architecture. Children aged 13 and under will need to have an adult kayak with them, but 4 year olds and up can go in a tandem kayak with an adult. It’s a great way to see the river and try something different.
Urban Kayaks allows you to do this while taking in the sights of the stunning city skyline. Whether you choose to take a guided kayak tour or paddle at your own speed, kayaking is an exciting way to see the Chicago River while getting a workout.
As a first-class travel destination, Chicago combines its rich history, breathtaking architecture, delicious food, and unique cultural offerings. From short weekend visits to long extended stays, there is no shortage of things to do, see, and experience. Plan well, travel safe, and enjoy the journey.
