Category

Things to do in Chicago

A group of people on a food tour standing in front of Lou Malnatis sign.
24
Jul

Must-Try Chicago Foods: The Iconic Dishes to Eat When Visiting

Discover the must-try foods that define Chicago, from deep dish pizza and Chicago-style hot dogs to Italian beef, tavern-style pizza, neighborhood favorites and sweet local treats.
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chicago riverwalk at night.
29
Jun

Things to Do in Chicago at Night: A Local’s After-Dark Guide

Skip the tourist trail. Discover where locals actually go in Chicago after dark, from night bike tours and live jazz to late-night deep dish, rooftop bars, and neighborhood bar crawls.
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Tourists on a 3 day itinerary at the chicago riverwalk with rainbow in background.
24
Apr

The Perfect 3-Day Chicago Itinerary: Food, Views, & Must-See Spots

Plan the perfect 3 days in Chicago with this easy, step-by-step itinerary. Discover top attractions, local neighborhoods, must-try foods, and the best ways to experience the city in a long weekend.
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Aerial view of Oak Street beach in Chicago.
19
Mar

Best Beaches in Chicago: Where to Swim, Relax, and Kayak

Chicago’s lakefront is packed with incredible beaches perfect for swimming, kayaking, and relaxing in the sun. This guide covers the best beaches in Chicago, when to visit, what to expect, and where to find rentals and hidden local favorites.
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Summer camp in Chicago.
05
Feb

What to Expect at Summer Camps in Chicago: A Parent’s Guide

Chicago offers an incredible variety of summer camps and programs for kids of all ages. This parent’s guide breaks down what to expect at summer camps in Chicago, including schedules, activities, safety, and how to prepare your child for a fun and active summer.
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Millennium park at night in Chicago.
12
Dec

Half-Day vs. Full-Day in Chicago: How Much Can You Really See?

Short on time? This guide breaks down the best things to see in Chicago with half-day and full-day itineraries, must-eat foods, iconic landmarks, and top Chicago tours.
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Sunset over the Chicago skyline.
17
Nov

Things To Do In Chicago On Your First Visit

Planning your first trip to Chicago? This guide highlights the must-see landmarks, lakefront views, neighborhoods, and foodie spots that make the city unforgettable—plus the best ways to explore them on bike or foot with Bobby’s Bike Hike. Get ready to experience Chicago’s icons, flavors, and hidden gems all in one seamless adventure.
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Chicago chinatown buildings.
12
Nov

Navigating Chicago’s Chinatown Restaurants

Chicago’s Chinatown is packed with dim sum hotspots, hand-pulled noodles, bold Sichuan flavors, and hidden gems only locals know. After guiding thousands of guests through the neighborhood, we’ve rounded up the best places to eat, what to order, and how to explore Chinatown like a pro. Come hungry — this is your ultimate guide to...
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group of 4 women posed in front of a decorated christmas tree enjoying a walking tour of Chicago's downtown festive holiday attractions while it is snowing
28
Oct

Chicago Holiday Guide: Best Lights, Festivals and Holiday Markets

Discover Chicago’s best holiday lights, markets, and festivals from Christkindlmarket to Lightscape, plus festive walking and food tours with Bobby’s Bike Hike.
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View from inside Wrigley Field in Chicago.
29
Sep

A Local’s Guide to Wrigleyville: What to See, Eat, & Explore

Planning a trip to Wrigleyville? From Cubs games at historic Wrigley Field to iconic restaurants, lively bars, and neighborhood attractions, our guide covers the best things to do in Wrigleyville, Chicago. Find out when to visit, how to get there, and top spots to explore.
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