Find the best half day tours in Chicago on Pelago. Plan and book online with the best prices and world class support.

The Best Half day tours in Chicago | Updated December 2025

Chicago

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Explore Chicago’s unique Pedway system featuring charming holiday decorations and iconic sights including Macy’s stunning Tiffany Ceiling and Millennium Park's festive tree and Cloud Gate sculpture.

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Savor iconic Chicago-style hotdogs while exploring the city's rich food history. Experience hidden gems and famous eats all while discovering downtown landmarks and enjoying a unique culinary adventure.

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Savor iconic Chicago bites while surrounded by vibrant conversations and local charm highlighting the city's rich culinary history and engaging culture. Each dish tells a unique story.

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Experience the charm of the Christkindlmarket where delightful treats like roasted nuts and gingerbread fill the air creating the perfect backdrop for a memorable holiday escape in Chicago.

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Experience Chicago from a unique angle gliding along the river as the skyline reveals its architectural marvels each turn uncovering stories behind the city’s most iconic landmarks.

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Experience the stunning architecture of Chicago's Millennium Park where innovative designs meet urban landscapes showcasing the city's rich cultural identity and inviting exploration.

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The Best Half day tours in
Chicago

The Field Museum of Natural History: Entry Ticket

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Holiday Walking Tour: Underground Chicago via the Pedway

Chicago Favorites Ultimate Food and Walking Tour

Chicago in a Day: Food, History & Architecture Walking Tour

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Chicago's Chinatown Food and Walking Tour

Chicago Pizza Tour

Bike Tour of Chicago's Lakefront Neighborhoods

Chicago's Ultimate City Bike Tour

Chicago Private Custom City Tour with Hotel Pick Up

The Field Museum of Natural History: Pass

Chicago-Style Holiday Hike: Festive Food and Walking Tour

Chicago Premium Driving Tour with River Boat Cruise

African American Heritage Tour of Chicago

Navy Pier Centennial Wheel Tickets

Private Chicago Foodie Tour

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

Chicago 6-Hour City Tour by Sedan