The Best Tips for a Weekend Getaway to Chicago Fun

This post may contain affiliate links which pay us a tiny commission. This is how FreebieNest is able to operate free of charge to users.
Advertisement

The city proper, popularly known as The Windy City, is the third most populated city in America’s union. There are numerous things to do, sightseeing and entertainment in Chicago as it is a city with culture, beautiful building designs, fabulous art, and amazing foods. Whether the reader is a newbie in traveling or has spent considerably more energy journeying through the world, the guide outlines some of the greatest things to do over the weekend in Chicago, including areas to dine and accommodations.

Attractions in Chicago

Downtown Chicago: Heartbeat of the City

Another recognized fact that tourists listen with interest and delight is the fact that it is always interesting and exciting to visit the downtown of any big city, and Chicago, of course, is not an exception too. Taking a self-guided walking tour of downtown Chicago, one can explore the sites and attractions of the city and the state in their own time and pace.

Here are some must-visit spots:

Millennium Park and The Cloud Gate Sculpture Millennium Park is a city attraction that one must visit, especially for first-time visitors in Chicago. This park is famous for the sculpture Cloud Gate, also known as ‘The Bean,’ and is lively, and a perfect beginning to your tour of downtown. The Bean is a steel structure that guests can walk around and even touch, and the silver reflective surface allows guests to take interesting pictures with the skyline of Chicago as the background.

Navy Pier The Navy Pier is a cement flying buttress stretched to about 3,300 feet that extends from the shoreline of Lake Michigan. There is also a Ferris wheel, movie theaters, restaurants, and shops incorporated as some of the viable assets of the project. Indeed, the pier is equally good for day activities as well as night activities due to the wonderful view of the lake and the city at large.

Riverfront District Chicago Riverfront is situated in the Riverfront district, where there are cafes, bars, fountains, and statues beside the river. Relax by the riverbank and enjoy a walk, or for an architectural view, take a boat ride that will show amazing views of Chicago from the river.

Willis Tower: Skydeck Experience Originally named Sears Tower, the Willis Tower is still one of the tallest structures in the western half of the globe. Going to the Skydeck on the 103rd floor is thrilling, and if one has the guts, stepping on The Ledge, which is a glass flooring that protrudes 4 feet outside the building. The views of the city are splendid and beautiful and offer a good opportunity to take a picture.

Medinah Country Club: Golfers will be in Seventh Heaven In regards to golf lovers, one place that they should not miss is Medinah Country Club. This club, situated in one of the chives of Chicago, has been home to several international golf tournaments, including the Ryder Cup. However, even for the non-golf enthusiast, the wonderful situation of the area and the rather interesting history of the club is enough of a reason to visit.

Restaurants in Chicago

Lou Malnati’s Pizza: Deep American Pizza

Even if the experiences differ from what one may expect, it is recommended for a slice of genuine Chicago-style pizza.

Krispy Kreme Donuts: A Wonderful, Yummy, and Scrumptious Start to Your Day

Of course, you can never go wrong with starting early in the morning with some delightful meal that will not only fill your belly but also kick start your rusty metabolism. Krispy Kreme is indeed a chain but it is a lovely place to grab breakfast, especially if you can come when the “Hot Now” sign is on. This tells you that fresh donuts are prepared immediately for you, and a free hot donut could melt in your mouth immediately. This is especially an enjoyable experience to witness the preparation of the donuts for you and your family.

Carnelli’s Delicatessen: Sandwich Heaven

Carnelli’s Delicatessen can be found in the food court of Navy Pier, and it offers really good portions of food to grab and go. Made with different breads, their filling choices are well-loved by the locals and foreigners who have taken their time to dine at the restaurant. This is a great place to grab something to eat before further viewing the area of downtown Chicago.

Accommodations in Chicago

Luxury Hotels

For the businessmen and tourists who want to enjoy the touch of class in Chicago, different chic hotels are available to give the visitors the best experience. The Peninsula Hotel on The Magnificent Mile offers elegant rooms, gourmet food, and a spa. A second great option is the Waldorf Astoria Chicago; luxury and comfort are set in the sophisticated Gold Coast area.

Budget-Friendly Options

Any frugal traveler will have no scarcity of low-cost options when it comes to accommodations in Chicago. The Freehand Chicago is located in the River North area and has private rooms as well as dorms for backpackers and small groups. Another good choice is the HI Chicago Hostel, where the traveler can find cheap but very comfortable accommodation near Grant Park and the Art Institute of Chicago.

Family-Friendly Stays

Families traveling to Chicago will benefit from hotels such as the Embassy Suites by Hilton Chicago Downtown Magnificent Mile. The newly renovated suite in this hotel is very large, inclusive breakfast is available, and there is an indoor swimming pool that will make the children happy. Family-friendly with kitchenettes and located in the heart of Chicago is the Residence Inn by Marriott Chicago Downtown/Loop.

Ways on How to Get the Best out of Your Weekend Trip

Plan Ahead

Chicago has so much to offer and is a very dynamic city, meaning that it is always important to have an itinerary when going for a weekend in the city. Come up with a schedule outlining the places that are on your checklist but do not overstuff your day with plans. It is advisable to buy the tickets ahead of time, especially for activities such as the Skydeck, in order not to spend a lot of time in queues.

Use Public Transportation

Public transport, which in this case is CTA, the public transport system of the city of Chicago, is well-developed and affordable. You do not need a car because most points of interest are addressed directly by bus or the “L” train. It is advised to possibly buy a CTA pass for tourists for unlimited access during the trip.

Explore Beyond Downtown

Nevertheless, do not get lost in the city center and its opportunities – discovering the peculiarity of the Chicagoan districts is a must. The places of interest include Wicker Park, Lincoln Park, and the West Loop, among others. Each has a unique ambiance featuring different restaurants, shops, and touristic sites.

Enjoy the Outdoors

Chicago is located on the shores of Lake Michigan, and there are many outdoor activities to enjoy. Take a leisurely stroll in one of the beautiful parks in the city, for example, Grant Park or Lincoln Park. If it is hot, take a swim or spend some time at the shores of Lake Michigan or anywhere you find comfortable.

Take in a Show

Chicago, being one of the most popular tourist destinations, is very famous for the theatre where a number of theatre troupes are found. Whether it is Broadway shows at Chicago Theatre or the Improv Comedy at The Second City, it has something for everyone. Look in the directory and try to see if you can get tickets to one during your stay.

Savor the Food Scene

When it comes to food, Chicago’s cuisine varies with an extensive and tasteful variety for every food enthusiast. Besides tasting deep-dish pizza, you must also include other Chicago specialties like Chicago-style hot dogs and Italian beef sandwiches. You will not be left short of options for good food since the city boasts restaurants that are classified as Michelin star restaurants to simple cafes.

Conclusion

A weekend trip to Chicago would prove to be an exciting break from regular routine, and the fixtures to be seen, foods to be tasted, and comfort of the hotels to be enjoyed all deserve a shot. From the sights in downtown to the rich food experience up to the comfortable accommodation that you could find in Chicago, the city is indeed for everybody. Book now and find out more why Chicago, tagged as “The Windy City,” is a favorite tourist destination.