5 Ways Groups Can Travel Around Chicago

So you’re planning your next big Chicago outing, and you have a larger-than-average group in tow. Whether it’s a sightseeing tour with out-of-towners or a night out with 10 of your closest friends, having a reliable transportation plan is a must.

Not sure how to navigate Chicago with a group? Here are some transportation options to keep in mind as you plan your next event or excursion:


Charter Bus Rental

Hands down, a Chicago charter bus rental is the most efficient way to keep a group all together and comfortable when traveling in the Windy City. Motorcoach rentals can range in size from 56-passenger charter buses to 18-passenger minibusses—plus they can offer comfort-minded amenities like plush seats, WiFi, luggage storage, and ADA-compliant features like wheelchair lifts. Not only do motorcoaches provide comfortable travel accommodations for one-time sporting event trips and Chicago wedding shuttles, but you can also reserve long-term rentals for transportation circuits to and from the office, regular corporate events, or private Chicago tours.

The catch? Renting a charter bus has a high up-front cost unless you decide to split the cost of your reservation amongst your passengers. That being said, some Chicago charter bus rental companies like GOGO Charters offer transparent pricing that’s personalized for every trip, so your group can know precisely how much you’ll need to budget before you embark.


Chicago Public Transit

Known as the “L” to locals, the Chicago Transit Authority offers extensive rail services throughout its most-frequented neighborhoods. Major attractions can be found along the Loop (the elevated rail that encircles Downtown), including the Cloud Gate in Millennium Park and the Willis Tower. And with fares averaging at $2.50 per person with free transfers, Chicago’s public transportation is an affordable way to get around the city like a local.

That being said, traversing any city’s public transit system can be a challenge with a large group of people, especially if you’re traveling with folks who are not familiar with the L. While smaller groups of travelers should have no trouble sticking together and making transfers with ease, a larger headcount makes it more likely someone will get lost. Make sure your routes are carefully planned and memorized by your travelers before you step on the train, or consider another group transportation option if you’re traveling with more than 6 people.


Chicago River Water Taxi

Planning to cross the Chicago River during your group outing? Hopping aboard a water taxi is a fun, only-in-Chicago transportation method and a great way to avoid congested roadways during peak rush hours. Each group member can purchase an all-day pass for about $10 per person, and passengers are permitted to bring luggage and food aboard the water taxi. Keep in mind that not all vessels are climate-controlled, so dress accordingly during the hot summer months or when the chilly wind picks up off Lake Michigan.

Taxis and Rideshare Apps

When it comes to on-demand, point-to-point transportation, hailing a cab, Uber, or Lyft is a great way to get around Chicago if you’re not on a set schedule. Especially if your group is flying into or out of O’Hare International Airport, at-will transportation services are quick and convenient for small groups of 6 that can fit into one vehicle or larger groups who don’t mind splitting up.


While these modes of transportation can be convenient—they can go anywhere there’s a road, after all—one limiting factor that may discourage some travel groups is pricing. Fares for taxis and rideshare companies are based on traffic conditions and time of year, which means pricing can spike during major events or around heavily-trafficked areas. So if your festival-goers need a ride back to the hotel after Taste of Chicago or your shoppers are ready to head home after a day at Navy Pier, you won’t know exactly how much your group transportation will cost until after the trip is done.

Getting Around Chicago

Whether you take the Loop to your favorite sightseeing spots, hail some cabs between event venues, or opt for a plush charter bus rental from the likes of GOGO Charters or National Charter Bus Chicago, there are a variety of ways to traverse the Windy City that suit a wide range of group sizes and itineraries. As long as you take your group’s size, schedule, and specific amenity needs into account as you start planning your group transportation, your Chicago group travels are sure to go off without a hitch!