Chicago Staycation Ideas: Summer Savings Guide

After weeks and weeks of staying inside, it's finally time to get out in the world again! Of course, safety and budget still being a concern, you may have thought a vacation was out of the question — think again! One of America's greatest cities is a short drive away. Use this guide to find great deals, understand safety measures, and have fun!

Chicago Staycation Ideas: Summer Savings Guide

It's finally time to get out in the world again! Safety and budget still being a concern, you may have thought a vacation was out of the question — think again! Use this guide to find great deals, understand safety measures, and have fun in Chicago!

The Hot List

Visit Chicago Staples

Sure, rooftop views are amazing, but there's nothing like taking in the city from 103 floors up! This summer, head up to Skydeck to take in the breathtaking views of Chicago.


Chicagoans love to eat! Which means there are so many amazing place to choose from. Let some of these deals entice you to try one or more restaurants on our list.


From the first tour to many, many skyscrapers later, their award-winning Docents continue to share Chicago’s iconic Architecture with guests from around the globe.


Chicago is synonymous with brunch and Yolk is a choice destination for some scrumptious pancakes, deliciously drippy eggs bennie, and delightful omelettes. With several locations in the city and surrounding suburbs, there's sure to be one near your hotel!


Summer is all about having fun and trying new experiences and with many of Chicago’s best attractions offering amazing deals, it’s so easy to fill your calendar. Take a look!


If shopping new stores and old favorites sounds like your kind of vacation, then you absolutely need to add these stops to your Chicago Bucket List!


Don't get left out.

Staycation Vibes

Outdoor Fun at Maggie Daley Park

Maggie Daley Park: a gorgeous destination for summer outdoor fun in the Windy City. This park is a great space to utilize for recreational activities for all. Whether you are looking for a family outing, a date, a picnic, some alone time, this space could be the perfect spot for you. 

Snack Attack: Don't Miss this Chicago Favorite

Since 1949, Chicagoans have been lining up to get their Garrett Popcorn fix and leaving the home-grown popcorn shops with cheddar dusted fingers and bags of goodness that will undoubtedly be empty before they even get back home. Find out where you can get your tin!

Chicago Architecture Center is Waiting for You!

This nonprofit cultural organization's mission is to inspire people of all ages to discover why design is important. They have done this for more than 50 years through tours, exhibitions, programs and events. Although 2020 may look a little different, it has not stopped them!

Explore St. Charles for the Perfect Getaway

Less than an hour’s drive west from Chicago is beautiful St. Charles! This city getaway has so much to offer for anyone looking to shop, eat, and relax. The beautiful Fox River runs through it making it a great destination for couples and families alike! Click through to start planning your perfect vacation.

Can't Miss Restaurant List

There are so many delectable cuisine options in the Windy City. We have drawn up this list of amazing restaurants in the Chicagoland area by category. Some of these scrumptious restaurants appear in various categories, so you can check off multiple cravings at once!

5 Great Reasons to Road Trip to Chicago

Traveling looks different this summer, but that is not something to be upset about. With one of the nation’s best cities located in the midwest, the summer vacation you weren’t expecting is just a short drive away. 

6 Outdoor Cafes To Add To Your Summer Bucket-List

With so many amazing places to choose from, it can sometimes be overwhelming to pick a summertime lunch spot with thousands of outdoor cafes around the city. Luckily, we’ve done the research and have come up with six outdoor cafes to visit this summer.

Don't get left out.

Exploring Chicago

Spend a Day on the Water! - Find out all the ways you can get on the lake on your next trip.

Lincoln Park Zoo - Find out why people come back year after year. Did we mention admission is FREE?

Chicago's Reopening Phases - What do they mean and what it means for your trip.

Your Weekend in Chicago Itinerary - If you and your partner are in need of a weekend away, head to Chicago!

Five Places to Explore Nature Around Chicago - City living isn't all concrete and steel. Discover some hidden escapes!

Outdoor Tours Perfect for Summer - If you're short on time, a tour is the best way to get the most out of your trip!

Family-Friendly Activities to Take Advantage of - Tired kids are the best behaved kids!

An Afternoon Downtown: What to Do, Eat, and See - If you're only here for a day, we have your itinerary waiting.