by | Published:

Pros And Cons Of Traveling With Friends To Chicago

America’s third-largest city has been described in a myriad of ways throughout its lifetime. And it’s not surprising. This city is one of the most impressive and multifaceted in the world. Though Chicago was known as a city of industry, it is very friendly for tourists, and there are plenty of memorable and enjoyable places to visit. Today, Chicago remains just as diverse, boasting a thriving arts scene, various shopping districts and the city of skyscrapers and public art absolutely worth admiring.


The question is what’s the best way to visit Chicago – solo, with your family or in a friend’s company? Though going traveling in your friends’ company sounds great, there are many things to consider. You may not prefer traveling alone, but how to choose a friend to travel with? Mind that you’ll feel more comfortable with a person having common interests and similar budgets. As most often disagreement between travelers appears about how much to spend and what to do. That’s why before traveling with a person for the first time, ask him or her about travel habits – at least to know what to expect.

The question – what transport to choose while traveling around the city – is also worth considering. Thus, it is obvious that traveling with a friend to Chicago you can rent a car and split gas and vehicle rental costs. And, moreover, if you’re a member of a traveling group, you could consider different cars for rental and choose something spacious, e.g., 6 passenger car rental at O’hare Airport.

Best Time To Visit Chicago

It is often said that Chicago has chilly, windswept weather, but it’s not quite true, for most of the year, the city offers comfortable temperatures for spending time outdoors.  


Visiting Chicago will please you the most in spring and in autumn, when the temperatures are warm and you can enjoy its architectural and natural pleasures — many of which are free. Also, during this period the metropolis, built on 22 miles of Lake Michigan’s southern shore, provides a variety of festivals. However, the peak of tourist and festival season is in summer, when Chicago is full of travelers hoping to take advantage of the warm weather and abundant activities.

How To Spend Less Traveling With Friends To Chicago

Most of your budget will go to housing, so you will want to be discerning about the timing of your trip. Rates usually change with the seasons (prices are higher when the weather is better) and also depend on business traffic (midweek rates can rise dramatically). 

Here Are Some Top Tips On How To Save Traveling In Chicago:

Choose The Right Place To Stay

It is more reasonable to choose less-known hotel options e.g. in Old Town or Lincoln Park, especially if they are conveniently placed by one of the elevated (the L) or subway train lines. 

If you are a business traveler and stay on the company dime, you will go to one of the hotels in the Loop. North Side neighborhoods like Lincoln Park and Lakeview cater to visitors that are more down-to-earth. Here you can find more affordable places to hang your hat. So, check out the bed-and-breakfasts options over here. 

Mind that even though during the winter months the weather outside may be far from pleasant, there are plenty of deals regarding dwelling places to be found. Many hotels cut their rates, and cheap flights are easy to get.

Buy Access Pass

Consider investing in an all-access pass, which will help you save a lot on your entertainment expenses. The Go Chicago Card and Chicago CityPASS grant access to the most popular attractions of Chicago for one set price. 

Getting Around Chicago

One of the most economical and therefore the best ways to travel around the city (including to and from the city airports), is via public transportation – specifically riding the L train. Besides this way to get around Chicago is also the most scenic.


The L or “elevated train” is quite cheap, accessible and convenient, also since it cooperates with an extensive bus system, which routes service to nearly every attraction.  The Metra regional train system making stops in Chicago, neighboring cities and its suburbs is also available. There’s another option – cabs and ride-hailing services – also available, but a bit expensive as it has high starting rates and extra charges. However if you do drive you could easily substitute cabs by cars for rental – rental agencies can be found at both airports.

Things To See And To Do In Chicago


As we have stated at the beginning this fantastic city is full of wonderful and enjoyable places to visit. The most convenient way to flatter the most number of attractions is to take one of the vast diversity of available tours. There are dozens of the best tours of Chicago, including walking tours, bike tours, food or even brewery tours. You can choose one of the guests’ favorites: the Chicago Architecture Foundation’s boat tour along the Chicago River or the Must-See Chicago walking tour. Many visitors pick a self-guided tour of the best public art. Remember that speaking of Chicago there’s nothing “too touristy” about taking a tour.

Leave a Comment