Also see our other holiday gift guides:
- Something for everyone
- Personalize it!
- Custom photo gifts
- The gifts that seem inevitable for the 2025 holiday season (a work in progress)
We love Chicago. Always have and always will.
Millions agree with us—and if your holiday gift-giving list includes at least one Chicago lover, this gift guide is for you.
What is there to do in Chicago?
Locals and tourists have a grand old time just walking around the city and many of its hallowed suburbs. But if it’s structure you’re looking for, there’s the Chicago adventure bucket list.
It’s a collection of 50 cards meant to be scratched off to build in some suspense about where to go next that’s uniquely Chicagoland. Famous landmarks, hiking trails, hidden gems loved by locals, museums, historic sites, escape rooms, riverboat tours all are included.
Great idea! We agree with reviewers who say that including coupons for discounts would be a natural enhancement to offset the price of the cards.
For a more conventional approach to exploring, there’s also the “Chicago Travel Guide 2026.”
Loving/hating the CTA around the holidays
Anyone could drive or take an Uber but the authentic experience is to ride one of the Chicago Transit Authority (CTA) buses or trains.
Chicago is one of the few cities in the world—along with only New York and Copenhagen—to offer 24-hour train service on major lines (Red and Blue).
You have many options to help your intended celebrate the love/hate relationship riders have with the CTA.
The CTA train sign above, an example of the full set of stops available, is printed on a poly/cotton blend canvas. It’s 50.5 inches high and 8.5 inches wide. Customization is available on request from Chicago-based The Frame Shop.
Even the most hard-nosed Chicagoan can’t resist a surprise sighting of the festively lit CTA holiday train, whose runs are memorialized in this fun 2025 book by photographer Daniel Moreno.
As an aside, the original name of the jazz rock band Chicago was Chicago Transit Authority. And so, it seems only natural to mention the Chicago XXV 25 Christmas album featuring their signature brass and all the Christmas classics.
Before we move on, for those who live outside the city but identify as Chicagoans, clothes (shorts and caps) featuring their Metra options—Burlington Northern Santa Fe, Chicago & Northwestern, Rock Island and Milwaukee Road—also are available, as are shirts for various station stops (e.g., La Grange Road).
Nod to the city of neighborhoods with this set of two glasses featuring maps of the neighborhoods.
2025 books in awe of the architecture
If the distinctive architecture of Chicago is of specific interest, the last 12 months have seen the publication of many fine books that would enhance any Chicagophile’s library.
At times, Chicago has been home to buildings that have been the tallest in the world, the largest as measured in square footage, and the most beautiful thanks to their decorative ornamentation. “Chicago’s Greatest Buildings”celebrates those and more as author Ellen Shubart describes 84 buildings that have evolved the city’s architectural heritage.
The Wrigley Building is Chicago’s most recognizable tower, “the high-water mark of Beaux Arts Classicism in the city, a gleaming white palazzo at the head of Chicago’s Michigan Avenue”aka the Magnificent Mile. Almost 400 pages, “The Wrigley Building: The Making of an Icon”includes 400 rare images with untold stories of designers, dreamers and cultural revolutionaries.
“Chicago Homes: A Portrait of the City’s Everyday Architecture”is the definitive, illustrated guide to Chicago residential architecture, including housing styles and types unique to the city. Written and illustrated authoritatively by Chicago insiders Carla Bruni and Phil Thompson, this would be a perfect gift for a Chicago-area Realtor, among others.
Originally built in 1929 and used for salt storage and processing, the Morton Salt Shed for decades was a familiar Chicago landmark along Elston Avenue between Division Street and North Avenue. Recently, the building was repurposed and transformed into a stunning music venue.
From photographer and writer Sandra Steinbrecher, “The Salt Shed: The Transformation of a Chicago Landmark”tells the story of the deconstruction, reconstruction, and reinvigoration of this classic, industrial Chicago building.
See it all—Willis Tower, the Hancock Building, Navy Pier and lesser known spots—from the sky in “Above and Across Chicago,”published in 2024. The book is 200 pages of gorgeous aerial shots taken in all weather conditions by multiple talented photographers.
Celebrate the cuisine
Something else to celebrate about Chicago is its celebrated cuisine.
Of course we’re going to start with pizza!
A party pack of three (each) Lou Malnati’s legendary deep dish pepperoni and sausage pizzas arrives cold and can go from box to table in 40-ish minutes. It’s shipped on ice in a signature Malnati’s box. We know a certain homesick surgeon relocated to Winston-Salem, N.C. who lives for such periodic Malnati’s infusions.
Who makes the best Italian beef in the city? The ongoing debate, triggered and fueled by the television series “The Bear,”consistently ranks Buona Italian Beef among the top.
This tub includes roasted beef, beef drippings and all the natural flavors and spices—just heat and drop a healthy serving on a French or Italian roll. The 3.19 pound tub serves about six. Ahh…
Other cities have popcorn shops, and some of them even sell the Chicago mix (caramel and cheese), but there’s nothing like Garrett’s.
Popcorn in hand, let’s go to the movies—specifically movies set or filmed in Chicago. Below are some classics, all of which are going to look even better on Blu-ray.
A Ron Howard blockbuster thriller following a family of Chicago firefighters.
A snapshot of a day in the life of a community hub on Chicago's South Side.
In the original, Macaulay Culkin as Kevin McCallister defends his home from bungling burglars after his family leaves him behind when they leave for a vacation. The family attempts another trip in Home Alone 2, but this time Kevin boards the wrong plane and needs to fend for himself in New York.
Starring John Cusack as a miserable record store owner in Wicker Park just as the neighborhood was transitioning from gritty cool to mainstream in the late 1990s.
A rom-com romp across many great Chicago locations, include O'Hare Airport, the old Comiskey Park and the Chicago River.
Mostly set in the suburbs (Highland Park), this iconic Tom Cruise's film includes an unforgettable L train scene.
Sandra Bullock stars as a CTA token collector who saves a man's life on Christmas Day and is mistaken for his fiancée. Included are real-life locations: the Randolph/Wabash station, since demolished; the L tracks at the Sedgwick station, Northwestern Memorial Hospital, Lake Point Tower in Streeterville, Logan Square, Portage Park neighborhood and La Grange.
Sweets for the sweet
Did you know that Chicago for decades was known as the candy capital of the world?
Its rail and freight capability, combined with a)easy access to milk and dairy from Wisconsin, corn syrup from Iowa and sugar beets from Michigan b)the cold weather and c)an immigrant workforce arriving with Old World confectionery skills all contributed to this dominance.
Mars Candy, Tootsie Rolls, Brach’s, Wrigley Gum (originally a premium included with mail-order baking powder sales), Fannie May and Frango all have roots in Chicago.
From its first store at 11 N. LaSalle Street in the Loop, Fannie May rose to fame with its signature buttercreams—which to this day no other U.S. chocolate maker can match. We say this based on our considerable, focused experience.
This sampler of mini pixies (a crunchy pecan and smooth caramel center enrobed in milk chocolate), mint meltaways and peanut butter buckeyes delivers three of the all-time classics. S’mores are relatively recent. And, don’t sleep on the exceptional eggnog creams, which are available just during the holidays.
This should be enough to tide someone over until they can cross the threshold of one of the dozens of Fannie May stores we are still lucky to have in the Chicago area, after ownership of the company transferred to the Italian confectioner Ferrero SpA years ago.
Frango Mint Chocolates for 70 years were handmade in large melting pots on the 13th floor of the flagship Marshall Field’s store on State Street. Production has since moved and Marshall Field’s was acquired by Macy’s (don’t get us started) in 2005. Even so, many reviewers today continue to declare Frango mints as the best premium chocolate mint, now also available in dark chocolate.
Superbly representing the tradition of authentic Chicago-style cheesecake, Eli’s combines the best quality slow-cultured cream cheese, sour cream, sugar, Madagascar vanilla beans and whole eggs baked on a signature crisp all-butter shortbread cookie crust. The 9-inch cheesecake ships frozen, pre-sliced for 16.
Other flavors, including a double chocolate made with Ghirardelli chocolate, chocolate chip, and sampler also are available.
But Chicago isn’t just for chocolate lovers. Your gift can acknowledge the city’s candy tradition by giving the jujy candy made world famous by the Ferrara Candy Company.
Ferrara makes Lemonheads in Forest Park, the wildly popular Nerds Gummy Clusters in Bellwood, and Classic Nerds and Nerds Rope in Itasca.
Lemonheads, in fact, provide a transition to Chicago’s sports scene and to specifically the United Center and before that the old Chicago stadium. Longtime Chicago Blackhawks fans will remember Lemonheads’ high profile at the games, which included not just being sold at the concession stands but also sponsoring the Lemonhead Zamboni.
All was the result of a tight friendship between the grandson of Ferrara founder, Salvatore Ferrara II, and the Wirtz family, owners of the Blackhawks. The connection is largely gone since Ferrara’s death and the company’s subsequent sale of the business.
Support our teams
As the home to storied, championship-caliber professional sports teams, Chicago sports teams are nonetheless capable of regularly breaking fans’ hearts. Still in all, we believe…if not in the ownership, in the management; if not in the management, selected coaches; if not in the coaches, a few stars.
You can still buy Michael Jordan, Walter Payton, Anthony Rizzo, and Jonathan Toews jerseys, but let’s focus on the possibilities of the present.
Where our teams play always seems to be a perennial topic, with a decision on the Chicago Bears’ move to the suburb of Arlington Heights imminent.
Is now an opportune time to give a gift that commemorates the Bears in Soldier Field?
$381.00
$267.39
This 23″D x 22″W x 22.25″H end table uses 25 layers of engineered wood to create a 3D stadium effect, with LED lights to match the actual lighting of the stadium. The lights are controlled by an on/off switch on a removable cord. Pretty cool, especially for the sentimentalist.
For Blackhawks fans, we love this LED neon sign celebrating the team’s iconic logo. The sign measures 8 inches long by 8 inches wide. It’s powered by a USB cable and has five levels of brightness. Might be just what your intended needs to cheer for the next Bedard hat trick!
Similar lights are available for the Chicago Cubs, White Sox and Bulls.
‘We have a Pope’
If your intended also happens to be a Catholic, you can’t go wrong acknowledging the high honor the city received this year when one of our very own was named Pope. The first American pope came from Chicago!
Chicago celebrated as only it could—with Pope Leo-inspired hot dog, pizza and Italian beef discounts. And there was that iconic baseball shirt featuring the Pope’s staff as a bat in a retro Chicago White Sox design.
To give the occasion the gravity it deserves, we’ll call your attention to this biography. Written by Catholic journalist and historian Matthew Bunson and published little more than a month after the Pope’s election, it’s considered an authoritative portrait and a suitable way to mark the moment.
Independent retailers have even more ideas
This brings us to the end of our sweep of Chicago-themed gifts worth your consideration. In addition, we also want to provide a hearty referral to Chicago’s many independent businesses that offer unique ideas.
They include:
- Block Club Chicago, an independent, 501(c)(3) newsroom whose coverage of ICE in Chicago has been running circles around traditional media. They operate a Chicago-themed merch shop that also deserves Chicago lovers’ support.
- The Chicago local artists and Chicago souvenirs collection of the all-round fabulous Chicago Architecture Center (CAC) design store, which offers a 15% discount to members.
- CTAgifts.com is the official merchandise website for the CTA, offering its fun annual tradition of a holiday train and bus holiday light up sweater, a custom made L map shower curtain and Chicago Architecture Coloring Book, among many gift ideas.
- The Fig Tree, a West Loop shop we haunt in person for unique gift items year-round. We’ll call your attention to the Chicago collection and the many Pope Leo items, including bobbleheads in two sizes.
- Obvious Shirts, a T-shirt company founded in Wrigleyville by a man given to making obvious statements about our world champion 2016 Chicago Cubs (Jake Arrieta, Kyle Schwarber, Anthony Rizzo, etc.). The North Sider went on to diversify by adding the South Side team, more merchandise, other cities, other sports, including college. Our favorite Obvious shirt continues to be the Wrigley Field clock apparel. It serves as a stealth signal on the streets in Chicago and elsewhere. Those who know know.
- Among TransitTees’ offerings are the Portillo’s limited edition puzzle and an Old Style replica lightbox. And don’t miss all the Chicago Theater gift items.
Also:
- Neighborly Shop collections, made in Chicago
- Foursided Framing‘s Chicago gifts collection
- 606 Apparel with lots of neighborhood-specific wear
- Souvenir City Chicago, including its Al Capone offerings