Ideas For Quick Trips To Chicago

Chicago is a historic city that offers an abundance of culture and scenery. Even if you don’t have much time to explore, you can always enjoy a weekend getaway or day trip to Chicago. Whether you prefer to get around the city on foot or by bike, there are plenty of different day trip ideas for you to choose from.

Here are some of our favorite things to do on a day trip into Chicago.

Chicago Scenic Day Trip City Views

Explore the Chicago Lakefront Trail

If you’re free this weekend, why not go for a relaxing ride on the Chicago Lakefront Trail? If you don’t feel like cycling, don’t worry. The trail is also suitable for walking. 

The Chicago Lakefront Trail is the city’s first official bike path, and there are a lot of historic attractions to be seen while traversing it. For example, on the southern end of the trail, you will find the Museum of Science and Industry. As you pass through the halls of this museum, you will learn some interesting things about historical technological advancements and other scientific achievements.

That’s not all. You can also explore several scenic destinations along the Chicago Lakefront Trail, as the trail connects many of Chicago’s most vibrant parks and beaches. You can stop at your favorite one, or ride the entire 18-mile trail to see them all. The choice is yours! If you prefer to spend the night in the area, there are many local neighborhoods that can accommodate you.

Spending a day or two exploring the Chicago Lakefront Trail is a great idea for couples who enjoy spending time outdoors. Though, riding a bike or taking a walk through the city can be fun whether you are alone or with your family. But if you are planning to visit the trail alone and want company, there are many group tours that offer tours that run through the Chicago Lakefront Trail.

Chicago Public Art Displays

Discover Chicago’s Public Art Displays

There are hundreds of spectacular public art pieces located throughout Chicago’s interior. Many of the most awe-inspiring pieces are located in Chicago’s Loop, so you can easily see the best the city has to offer over the course of a weekend trip.

The pieces of public art that you can visit include sculptures, murals, street art, and graffiti. A variety of different artists from around the world contributed to the creation of these magnificent pieces of art, and you can go appreciate them at no cost. 

Here are some popular art attractions you can visit while in the city for a weekend getaway.


In 1993, artist Richard Hunt designed a massive stainless steel sculpture that is designed to abstractly represent the tension between the natural and the industrial using a mixture of traditional and contemporary elements. 

The Chicago Picasso

Pablo Picasso is famous for producing spectacular pieces of art that are posted in museums and art galleries throughout the world. Chicago is home to some of his art as well, with one of his sculptures resting on Daley Plaza. 

The Bronze Cow

In 1999, Chicago’s Commissioner of Cultural Affairs organized “Cows on Parade”, an event that involved placing 320 life-sized cows throughout the city. While these cows were not permanent installations, you can still experience a piece of the unique event. The eight-foot-long Bronze Cow was donated to Chicago in 2001 as a way of commemorating Cows on Parade. 

Art Lovers Are Welcome In Chicago

If you love art, Chicago has many attractions that are sure to impress you. An art tour through the city can be shared by you and your significant other, or with a group of new friends from a local tour group. If you are interested in booking an art tour, try Chicago’s Ultimate City Bike Tour with Bobby’s Bike Hike Chicago. This tour will take you past several of the art attractions listed above, while also weaving in a mixture of Chicago’s other signature destinations. 

Chicago Emerald Necklace at Night

Ride Through Chicago’s Emerald Necklace 

Many of Chicago’s residents are not familiar with the intricate series of boulevards that comprise the Emerald Necklace of Chicago. Though, once you discover it, you will see why many of Chicago’s visitors choose to explore these neighborhoods on a weekend getaway. 

The Boulevard System of Chicago, or Emerald Necklace, is a network of historic landmarks that have existed since the late 1800s. You can ride a bike throughout the entire system, giving you the opportunity to discover many of Chicago’s most unique parks and other landmarks. This trip idea is a great option for couples or individuals who want a glimpse into the way locals live in Chicago. 

We’d recommend renting a bike and enjoying a cruise through the Emerald Necklace at your own pace. Bobby’s Bike Hike has a number of bike rentals to choose from, including electric, comfort, road, tandem and kids bikes. Bike rentals are available for rent by the hour, half-day or the full month if you’re taking an extended getaway to Chicago. All bike rentals include free bike lock, helmet and trail maps of biking paths through the city.

Whether you travel by bike or by foot, Chicago’s Emerald Necklace flows through several prominent neighborhoods in the city, so you can enjoy a laid-back day riding through well-kept residential areas. As you journey through new areas, you may even meet some friendly Chicago locals. 

If you have an entire weekend to spend in the city, you can book a hotel in the nearby Historic District of Logan Square Boulevards. The next day, visit Logan Square where you can enjoy some amazing food and experience a piece of Chicago’s vibrant nightlife. By the way, if you like burgers, we recommend brunch at Mini Mott in Logan Square.  

Grant Park in the summer in Chicago

Have a Picnic At Grant Park

A lot of Chicago’s biggest public events occur at Grant Park, a luscious attraction located in the heart of downtown Chicago. Though, even if there aren’t any events happening, you can still find much to do when visiting Grant Park on a weekend getaway to Chicago.

Grant Park isn’t only a park. There are many attractions to be found throughout the area. For instance, you can also visit Millenium Park or, if you have kids, Maggie Daley Park. You’ll also be impressed by Buckingham Fountain, and if you time it right, you can enjoy one of the city’s famous water shows. The Art Institute of Chicago is also located in Grant Park, so if you have an interest in arts and culture, that’s an option as well. 

We’d recommend either enjoying a picnic at Grant Park on the guided Ultimate City Bike Tour with Bobby’s Bike Hike, or renting a bike and enjoying an afternoon stop at Grant Park on your own self-guided tour. Bobby’s Bike Hike also has a number of bike rentals to choose from, including electric, comfort, road, tandem and kids bikes.

Chicago’s Ultimate City Bike Tour of Popular Attractions, Parks, and Museums

Depending on your interests, you may want to see all of these locations in a day or two. If that is the case, you may be interested in booking a guided tour through the parks. Chicago’s Ultimate City Bike Tour will take you through most of these locations in about three hours, leaving you plenty of time to have a picnic in the park once the tour ends. Book the Ultimate City Bike Tour today!

Tour Highlights Include:

  • Millennium Park
  • Chicago Theatre
  • Chicago Riverwalk
  • Buckingham Fountain
  • Grant Park
  • Field Museum of Natural History
  • Shedd Aquarium
  • Soldier Field
  • Northerly Island
  • 12th Street Beach
  • Adler Planetarium
  • Lakefront Trail

Chicago Chinatown at Night

Have A Cultural Experience In Chinatown

Most major American cities have a Chinatown, but Chicago’s Chinatown has a vibrant and exciting atmosphere that you wouldn’t want to miss out on. This lively business district is speckled with a variety of different businesses, including a number of gourmet restaurants and local bars. 

There’s so much to do in Chinatown that you may prefer to spend your whole Chicago weekend getaway there. This is especially true if you are traveling with a significant other, as this area holds many venues and things do to that could make for a fantastic date night. On day one, you can take a food tour of Chinatown and try the many traditional foods that are typically sold out. 

Chicago Chinatown Food & Culture Walking Tour

Like a Chinese menu, the sheer number of possible things to do in Chicago and in Chicago’s Chinatown on a weekend trip can be overwhelming. Fortunately, the experts at Bobby’s Bike Hike have created the perfect guided tour of the district. On the Chicago Chinatown Food and Culture Walking Tour, you’ll sample culinary delights from 5 distinct Chinese regions while learning interesting facts about China and the history of Chinese immigration. Whether you’re a first-time visitor or a Chicago native, the guided food tour of this thriving neighborhood will whet your appetite for another visit! Book the Chicago Chinatown Food & Culture Walking Tour today!

Tour Highlights Include:

  • All food samples are included in the ticket price. Guests can upgrade to the VIP package, which includes samples of plum wine, bubble tea and a specialty jasmine Chicago craft beer only served at Triple Crown.
  • Wentworth Avenue
  • Cantonese Cuisine
  • Dim Sum
  • Chinese Tea
  • Portuguese-Chinese Bakery Treats
  • Xi’an Cuisine
  • Lao Sze Chuan
  • Sichuan Chicken
  • Chinatown Square
  • Mongolian Hot Pot

A group on a bike tour of Chicago

Experience Chicago On a Guided City Tour

Whether you’d prefer to visit one of Chicago’s many parks or enjoy a night of drinks in Chinatown, this city offers endless opportunities for a good time. If you aren’t too familiar with Chicago, a tour can help you settle in and learn more about the city. You also might make new friends who enhance your overall experience. 

Bobby’s Bike Hike is the Top-Rated Food, Walking and Bike Tour Company in Chicago

If you want to see the city, feel free to book one of our Chicago city tours or explore the city on your own with a bike rental (electric, road, comfort, mountain, tandem and kids bikes available for rent). We just know there are tons of great options for how you can spend your weekend trip to Chicago, so make sure you give the place a visit soon!

Our Chicago Chinatown Food & Culture Walking Tour will take you through the Chinatown district, past many colorful shops, interesting monuments, and, most importantly, fantastic restaurants. 

You can also try our Ultimate City Bike Tour, which covers many of Chicago’s major attractions, including Millenium Park, Cloud Gate, Grant Park, Buckingham Fountain, and Navy Pier.