So you want to travel to Chicago? You are about to embark on the adventure of a lifetime. Chicago is full of many wonders, sights, and sounds, but here are some things you probably did not know you can do while traveling to Chicago:

Drop off your kids at a daycare

Traveling with kids can be many things- relaxing is hardly any of them. When parents are exhausted, it is a lot more challenging to enjoy the Windy City and all its glory. But with child-care included, everyone, especially the parents get the rare opportunity to enjoy the break they need.

The good news is that there is plenty of great childcare in the city, which will leave you free to experience the city sans tantrums and meltdowns. The majority of all-inclusive resorts all over the city already offer built-in childcare.

However, if your resort or hotel does not, you will have to actively look for a quality daycare where you can leave your little ones for an hour or two as you enjoy some much needed alone time during your vacation. You can also easily find someone to babysit while you enjoy a romantic dinner out or any other special event.

Shop till you drop during your Chicago trip

Chicago enjoys fair weather but that’s just one of the few reasons that you should pack light for your Chicago adventure. Trust us- not only will it make the overall travel experience so much less stressful for you, but it will also give you plenty of opportunities to hunt for bargains all over the city.

You already know that Chicago is a great city to visit, but what you may not know is that you’ll also find some of the best shopping options in the city. Case in point, Michigan Avenue, is known to be a prime shopping destination for the individuals arriving in drones in the city. However, it is not the only location where you can go for a shopping spree.

Some great locations to shop include Armitage Avenue, which is situated in a vibrant neighborhood known as Lincoln Park, or State Street which is lined with prime shopping locations for you to explore. It doesn’t matter if you are hunting for bargains with vintage buys or you are not afraid to burn some cash with some designer merch, there is something for everyone in Chicago.

Kayak on the Chicago River

If you are traveling to Chicago, then you must have heard about the impressive architecture river cruises that occur all over the state. And yes; they’re as fabulous and as indulgent as you imagine them to be. However, we understand that you are in the market for a different experience, which is why we highly recommend that you kayak on the Chicago River.

Several companies offer visitors guided trips that will give you an up-close and personal look at the city’s waters. These guided trips are designed to focus on the city’s history, the amazing architecture, and the guides will regale you with stories of the city’s ghosts and gangsters. And if you are in the market for a little more Va-va voom, you can even request firework paddles for an even more magical experience.

The great thing about kayaking experiences is that they are open to visitors of all ages and experience levels. The prices are friendly as well and range from $45 to $65. Please note that since you will be in the water, it is probably best to show up in comfortable attire. You will also need to make a reservation first.

Sample some of the best food that Chicago has to offer from Maxwell Street Market

At Maxwell Street Market, you will get everything from food and clothing to knick-knacks and souvenirs that you can take home with you. The Maxwell Street Market is situated on the Near West Side and it really does have things for every kind of traveler. The market boasts a rich history so if you are keen on interacting with the locals and learning some interesting city facts, this would be the place to do it.

Maxwell Street’s history can be traced all the way back to the 1800s. It was started by Jewish immigrants looking to sell their products but the market grew to become the modern flea market that it is today. While the market may not be as busy as it is during other travel seasons, it is a Chicago institution that is worth exploring, especially if you are still in the city on any Sunday.

Though you’ll go for the wares, you will probably end up staying for the wonderful food. You will dine on some of the best Latin and Mexican food that the city has to offer in this little corner of the Windy City. But if you want to sample as much as you can, we recommend signing up for a food tour.

During this tour, you will be guided by a native who understands the city’s restaurant and will probably take you to all the best spots. If you regard yourself a foodie, this a must-do activity if you will be in the city.

Learn what it felt like to be a Chicago gangster in the ‘30s

Chicago enjoys a vibrant history of organized crime. Some of the nation’s most prolific mobsters made their fortunes in the city. We’re talking about the likes of Moran, Dillinger, and of course, Capone. If this sounds like the sort of thing that would interest you, then you should definitely sign up for a Chicago mobster tour.

Not only will this allow you to experience parts of the city that you would never otherwise have experienced before, but you will also learn what the city was like back in the 20s and 30s when organized crime in the city was at its height.

Once you are done with the tour, why not ask your guide to point you over to a speakeasy for some cocktails? The city has secret bars that can be a little difficult for a new visitor to track, unless with some assistance from a local.

Final Thoughts

Chicago is one of the busiest places for tourists so you can be sure that you’ll have a great time from the minute you get there. If you or a friend is planning to travel to Chicago soon, you will appreciate these tips shared above as they will make your travels that much smoother and safer.


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