It’s the most wonderful time of the year! It’s the season to find thoughtful, creative gifts that come straight from the community you are proud to be a part of. To help you out, we’ve created this holiday gift guide for some of the best, locally sourced gift ideas that embody Chicago!

But first, we want to tell you about an important new initiative Bobby’s Bike Hike has started.

We believe in the importance of travel. Mark Twain wrote that “travel is fatal to prejudice, bigotry, and narrow-mindedness” and this is especially true for developing youths. However, we recognize that not everyone has the financial resources to travel and experince different cultures. To promote equity and inclusion in the travel industry, 25% of our gift certificate sales will provide low-income youth the opportunity to participate on a Chicago tour with a parent. 


Note: Some businesses and tours may be temporarily closed/postponed for a period of time due to COVID. It’s always best to check their official site for the most up-to-date information.

Local Chicago Holiday Gift Guide

Gift Ideas For The Foodie 

When we think of the holidays, the first thing that comes to mind is the food: candy canes, potato latkes, Christmas pudding, jelly donuts— YUM! Food is the cornerstone of culture, which is why the Bikes, Bites & Brews – Chicago’s Signature Dishes Bike Tour is an excellent way to explore the city of Chicago, with a cruise by Wrigley Field! Looking for additional Chicago foodie gifts? 

A tub of Garrett Popcorn carries the iconic mix of caramel and cheese popcorn that gives every bite a sweet and savory crunch. It doesn’t matter whether you’re a native Chicagoan or a visitor: everyone loves Garrett!

Got a pizza-lover on your holiday list? Gift them a deep-dish pizza from Giordano’s or Lou Malnati’s. Wait, what? Yup, that’s right! And the best part, you don’t have to live in Chicago to enjoy Chicago deep-dish pizza. They’ll ship their famous Chicago deep-dish pizzas all around the country, perfect for the pizza-lover on your gift list! Be sure to check out our blog on the best Chicago deep-dish pizza for a round of pizzas this season, or learn the truth about deep-dish pizza and how it became so iconic, for a full pizza gift idea.

Gift a subscription to First Slice Pie Café, for a friend living in Chicago. With this gift subscription, the recipient not only gets three delicious meals a week, but it also helps First Slice give out 750 meals a week to those struggling with hunger and homelessness.


Gift Ideas For The Cubs Fan 

Baseball is more than just a game, it’s an experience, especially in Chicago! Our the Bikes, Bites & Brews – Chicago Westside Foodie Bike Ride explores the patriotic energy of Wrigleyville, a neighborhood completely defined by the Chicago Cubs. If you like the Cubs even a little bit, you’ll grow to love them! If you know someone who’s a die-hard fan, there is no better gift than a spot on this tour roster! Check out these additional ways to rep the Cubs fandom.

Wrigleyville Sports has been located right across from Wrigley Field for 30 years, and they are loaded with merchandise! There’s nothing more magical than getting Rizzo’s jersey just a baseball pitch away from Wrigley Field.

A true Cubs fan doesn’t just wear the official merchandise. They also gotta represent Sluggers, arguably the most popular sports bar in Wrigleyville. What makes Sluggers so special? Well, we’re quite partial to the 2nd-floor batting cages! If your favorite Cubs fan keeps forgetting to wear their mask, Sports World has the solution… a huge variety of Cubs-themed masks. Long after the pandemic is over, your special Cubs fan will still be wearing the mask.

Photo of Wrigley Field by modonnell


Gift Ideas For The History Buff

The 1893 World’s Fair. The 1933 Century of Progress Exhibition. Marquette and Joliet. For people into history, there’s no better way to explore Chicago’s past and present than the Ultimate City Bike Tour. The name says it all. It’ll take you to the most popular and history-laden locations in the city! Here are some additional Chicago themed gifts to supplement the Ultimate City Bike Tour. 

There’s not a more iconic Chicago book than Erik Larson’s The Devil in the White City about the 1893 World’s Fair and hotelier/serial killer Dr. H. H. Holmes. Pick up a copy at Women and Children First, one of the largest feminist bookstores in the country.

If you have a friend that nerds out over urban transportation, they’ll love Loop: The Elevated Card Game and El: The Chicago Transit Adventure Board Game. You can find these games and other Chicago gift ideas at Transit Tees in Wicker Park and Andersonville! 

If you’re looking for a really, really, extra-special Chicago history gift, the Abraham Lincoln Book Shop will have the treasure you seek. In addition to the excellent historical books/items, one would expect, they also trade in valuable merchandise: rare documents from before the Chicago fire, artwork, sculptures, and even a Bible signed by Mary Todd Lincoln herself.

Photo of the 1893 World’s Fair


Gift Ideas For The Holiday Enthusiast

Can’t get enough of the holiday season? The best way to experience the holidays in Chicago is on the Chicago Favorites Walking & Food Tour. Situated in the heart of downtown, you’ll witness all the festivities and decorations. You’ll also have a full Chicago meal consisting of deep-dish pizza, Italian beef, and Chicago hot dogs! Here are our recs for the best holiday shopping and festivities in Chicago.

The most well-known collection of Chicago holiday shops is the Christkindlmarket. These German vendors sell exquisite ornaments and other delightful gifts. *The Christkindlmarket is all virtual for 2020, so you can get that Chicago Christmas shopping wherever you are.

If you’re looking to shop from a collection of local Chicago artists, check out the “One of a Kind” virtual holiday market. With over 300 artist booths to choose from, you’ll find the perfect, handcrafted gift! This marketplace is open through December 6.

It’s not really a stocking stuffer, but if you live in Chicago and haven’t gotten your tree yet, City Tree Delivery has your back. They make it easy by delivering the tree to your door, avoiding the hassle of hitching it up to your car and carrying it yourself. You can even have them help with the mounting/assembly!

Photo of Christkindlmarket by Doug Sun Beams


Gift Ideas For The One Who Has It All or When You Just Can’t Decide

Experiencing “analysis paralysis” over what to get for gifts this year? Give your loved one, friend, co-worker, frontline worker or whomever you please a Bobby’s Bike Hike gift certificate, and they’ll be guaranteed to find a Chicago experience they like. And even if they’re “not a tour person,” that’s not a problem! We also provide bike rentals by the day, week, or month, and are happy to help plan out a custom bike route. As a reminder, 25% of our Bobby’s Bike Hike Chicago gift certificate sales help lower-income youth access our tours.


We know that the holidays are going to look and feel a bit different this year. We hope this holiday gift guide helps you pick out the perfect holiday present so that even if you can’t celebrate in person, you can find a great way to say, “I love you.” And for those that are in Chicago for the holidays (this year or in years to come), check out our Chicago Holiday Guide to the local Chicago holiday lights, festivals, and markets.