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Bobbys Bike Hike
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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Highlight Foodie Photos from Best Chicago Food Tours
28
May

8 Best Chicago Food Tours in 2026: Deep Dish, Donuts & Biking

Chicago’s food scene is one to indulge in, especially when paired with the city’s rich history and iconic architecture. These are our recommendations for the best of Chicago food tours to add to your Chicago foodie plans.
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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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Group food tour photo on street in Chicago.
19
Nov

What To Expect on a Food Tour

Curious about what happens on a food tour? This guide breaks down everything you can expect—from tasting local specialties and learning the stories behind them, to discovering hidden gems with a knowledgeable guide.
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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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