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Chicago is my home-away-from-home. My sister lives here, which means I’m a frequent flyer (and driver) to Chicago. So I’ve got everything you need to know about how to visit Chicago.
The Ultimate Midwest Travel Guide
The architecture, museums, sports, food scenes, comedy clubs, and parks make Chicago a perfect vacation destination.
Here’s the ultimate guide for how to visit Chicago!
When To Go
June – August is Chicago’s peak tourism and festival season. Accommodation rates and crowds will be at their highest, so book hotels, Airbnbs, tickets, and tours in advance. These months are peak baseball season, so make sure you check if there are home games when you plan to visit. Home games will make prices and tourist numbers even higher. Average summer temperatures range from the high 50s to the mid-80s, so pack layers and be prepared for rain in August.
September and October are beautiful months to visit the city. The foliage will be changing, and the temperatures will be pleasantly cool (you’ll want layers for the mornings and evenings). Accommodation prices and crowds will be on the decline, and the city hosts an incredible Oktoberfest.
Winter is cold and windy with high snow chances, and winter lasts from November well into March (daytime highs are in the low 30s to high 40s, but wind chills can cause temperatures to drop into the negatives). If you’re okay with the cold, then you can score some great hotel deals in these months.
Spring is short and beautiful in Chicago. April and May have daytime temperatures between the high 50s and low 70s, and the city is covered in flowers. Make sure you have rain gear with you during these months. Prices and crowds will be on the rise, especially around Spring Break weeks, but you can still find some great accommodation and airfare deals.
What To Do
Explore Grant Park and see Buckingham Fountain (this fountain is turned off in the winter).
See The Bean at Millennium Park.
Shop (or window shop) on The Magnificent Mile.
Walk around Navy Pier.
Visit the Lincoln Park Zoo.
Take an architecture river cruise.
Explore the Garfield Park Conservatory.
Visit one of the city’s many museums.
Stroll along the River Walk.
Go to the top of the 360 Chicago Observation Deck.
See a comedy show.
Visit the Shedd Aquarium.
Go on a food and bike tour with Bobby’s Bike Hike Chicago.
Catch a Cubs, White Sox, Bears, Sky, or Bulls game.
Where To Eat
My Favorites: Proxi (Asian, $$), Monteverde (Italian, $$$), Aba (Mediterranean, $$), El Che Steakhouse & Bar ($$$).
Brunch Places: 3 Arts Club Cafe ($$), Blue Door Farm Stand ($$), The Brasserie ($$$), Little Goat Diner ($).
Rooftop Dining: Cindy’s ($$-$$$), Bar Avec ($$), Cabra ($$), Devereaux ($$$).
Pizza: Burt’s Place ($), Pequod’s Pizza ($), Pizza Friendly Pizza ($$), My Pi Pizza ($), Lou Malnati’s ($).
Fine Dining: El Ideas (American, $$$$), Momotaro (Japanese, Sushi, $$$$), Alinea (American, International, $$$$).
Asian: Roka Akor (Japanese, Sushi, $$$$), Duck Duck Goat (Chinese, $$-$$$), Le Colonial (Vietnamese, $$$$), RAMEN-SAN (Japanese, $$-$$$).
Best Viewpoints Of The City
Best Viewpoints Of The City
Cindy’s Rooftop Restaurant
Lincoln Park Bridge over the South Pond
Rockefeller Memorial Chapel Tower
Northerly Island
Wicker Park’s Northwest Tower
From a boat on the Chicago River or Lake Michigan
The River Walk
360 Chicago Observation Deck
Where To Stay
This city has some incredible hotels for every budget and preference. You don’t want to be driving a car around Chicago unless you have to, so choose a hotel that’s centrally located to public transportation and a majority of the activities you want to do.
So from chic high-rises to hotels where you can earn and use points, I’ve rounded up the best hotels in Chicago.
Chicago also has some incredible vacation homes!
Best Day Trips
Milwaukee, Wisconsin. If you want to escape Chicago to another big city, head to Milwaukee. Known for its beer and brats, Milwaukee is the perfect foodie getaway. Spend your day visiting the Milwaukee Public Market, hiking in Lakeshore State Park, doing a food and drink tour, and eating at Holler House.
Holland, Michigan. Every may, this Dutch-inspired town is home to one of the best tulip festivals in the country. You’ll find antique windmills, European architecture, beautiful gardens, and great bars.
Lake Geneva, Wisconsin. This lakeside town is famous for its Gilded Age vibes (think Great Gatsby in the Midwest). When you’re here, do a water activity, walk along the Lake Geneva Shore Path, sample wine at Studio Winery, and if you’re feeling adventurous, take a hot air balloon ride above the lake.
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Is there anything you’d add to this guide about how to visit Chicago? If so, let us know in the comments!
Plan The Rest Of Your Trip
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How To Visit Chicago
Recommended Tours in Chicago
Frequently Asked Questions
Is Chicago safe for tourists?
I felt very safe every time I’ve visited Chicago. But, as with any destination, you need to take precautions to keep yourself safe. Don’t walk by yourself at night, stay in a secure and well-located hotel or vacation home, use slash-proof, lockable, and RFID-protected bags and purses, and always have a charged cell phone with you.
What is the best month to visit Chicago?
June – August is Chicago’s peak tourism and festival season. Accommodation rates and crowds will be at their highest, so book hotels, Airbnbs, tickets, and tours in advance. These months are peak baseball season, so make sure you check if there are home games when you plan to visit. Home games will make prices and tourist numbers even higher. Average summer temperatures range from the high 50s to the mid-80s, so pack a mix of clothes and be prepared for rain in August.
September and October are beautiful months to visit the city. The foliage will be changing, and the temperatures will be pleasantly cool (you’ll want layers for the mornings and evenings). Accommodation prices and crowds will be on the decline, and the city hosts an incredible Oktoberfest.
Winter is cold and windy with high snow chances, and winter lasts from November well into March (daytime highs are in the low 30s to high 40s, but wind chills can cause temperatures to drop into the negatives). If you’re okay with the cold, then you can score some great hotel deals in these months.
Spring is short and beautiful in Chicago. April and May have daytime temperatures between the high 50s and low 70s, and the city is covered in flowers. Make sure you have rain gear with you during these months. Prices and crowds will be on the rise, especially around Spring Break weeks, but you can still find some great accommodation and airfare deals.
How do tourists get around Chicago?
It’s easy (and very enjoyable!) to walk around Chicago’s neighborhoods. But if you’re going to traverse the town, then you’ll want to use rideshares or the city’s metro lines.
Is Chicago an expensive city?
Chicago is a relatively expensive city to visit, but there are lots of free activities here. To save some money, visit on weekdays and during the shoulder of off-seasons, and eat out for lunch or prep your own meals.
How much is an Uber from O'Hare to downtown Chicago?
Because of Uber’s surge pricing, rideshares from the airport to downtown can range from $35-140 depending on the time of day. Pre-arranged taxis or shuttles can save you money and time when going from the airport to downtown. You can also take CTA trains (Chicago’s public transportation) to downtown for cheap.
Is it easy to drive in Chicago?
Not for visitors. Chicago’s packed streets, ever-changing road rules from hour to hour and day to day, stressful rules-of-the-road, and limited and expensive parking mean visitors should drive as little as possible while visiting Chicago (unless it’s to take a day trip).
How many days do you need to spend in Chicago?
Give yourself at least 4-5 days to spend in Chicago. This will give you plenty of time to explore some of the neighborhoods, enjoy the food scene, catch a game, see a show, and take a day trip.
Does Chicago have a beach?
Yes! Chicago’s 26 miles of scenic lakefront includes several public parks and gardens, an 18-mile Lakefront Trail, and more than two dozen free beaches. All Chicago beaches are open for the summer season from late May to early September.
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This guide about how to visit Chicago is not a sponsored post, and, as always, the thoughts and opinions expressed in this guide about how to visit Chicago are entirely my own. Some of the links in this guide about how to visit Chicago are affiliate links, and, at no cost to you, I may earn a small commission from this guide about how to visit Chicago.
