Chicago
Seasonal Activities

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Our most recommended Chicago Seasonal Activities

  • Chicago: Kayak or Paddleboard Rental with Optional Lesson

    1. Chicago: Kayak or Paddleboard Rental with Optional Lesson

    Rent a kayak or paddleboard and enjoy kayaking on either the Chicago River or Lake Michigan or paddleboarding on the calmer waters of Monroe Harbor on Lake Michigan. Choose to add on a paddleboard lesson. Take a skills assessment and watch a safety video upon arrival. If you don't pass the skills assessment, it is possible to partner with a more experienced friend. Enjoy on-site portable toilets and a changing room for your convenience. Single and tandem (2-person) kayaks are offered at both locations, while paddleboards are only available on Lake Michigan. Paddleboards are for 1-2 riders. The lakefront location in Monroe Harbor on Lake Michigan offers calmer conditions for both kayaking and paddleboarding and is perfect for beginners and families. More experienced kayakers can choose to kayak on the Chicago River, an amazing place to paddle, surrounded by spectacular architecture...

  • Chicago Holiday Season: Guided Walking Tour and Samples

    2. Chicago Holiday Season: Guided Walking Tour and Samples

    From shimmering lights to decadent bites, Chicago puts its best foot forward for the holidays.   Experience the city come to life during this special time of year on a walking tour through the Loop’s iconic holiday destinations. Pass by Millennium Park's ice skating rink and massive Christmas tree, admire the shimmering holiday lights on State Street, and behold Macy's dazzling holiday decor and window displays. Treat yourself with some brownies at the historic Palmer House Hotel, where brownies were invented, taste the famous Chicago deep-dish pizza and hot dog, and tuck into the city's largest open-air Christmas festival, Christkindlemarket, for some seasonal shopping. For an additional fee you can also enjoy a VIP Christmas cocktail sampling package.

    Kevin was a fun, informative and all around great guide. Highly recommend the tour for some Chicago Holiday fun!

Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

3.3 / 5

based on 11 reviews

Once again it paid for us to use GetYourGuide to book activities on the back of a booking.com hotel reservation.This walking tour was the highlight of our brief stay in downtown Chicago. Our guide Sarah was not only nice and knowledgable - she was enthusastic, approachable and genuine. We learned SO much we didn't know about Chicago! The walking pace was just right for exploring and talking together AND eating the amazing local snacks and specialties Sarah had organized for the group. I loved the cheddar and caramel popcorn mix while discovering the Pedway and the original-recipe brownie while soaking up the Palmer House. And we were especially pleased to have a slice of deep dish pizza waiting for us at Giordano's. (No need to spend the rest of our evening waiting 45 minutes to try it!) We highly recommend this tour.

Better than anticipated

Sara was an absolute delight. Knowledgeable and shared personal stories of places we stopped. Food was wow! Couldn’t eat the rest of the day. Would do another walk.

Kevin was a fun, informative and all around great guide. Highly recommend the tour for some Chicago Holiday fun!