Holiday Shopping Downtown: Treat Yourself While Checking off Your Gift List

chicago shopping
It’s time for holiday shopping, and you’re still in a merry mood. You enter the first store smiling as you browse for the perfect gifts, imagining the grins that light up your loved ones’ faces as they open your perfectly-selected presents.

Yet, with every passing moment your spirit diminishes just a little. By the end of the day you’re sneering at strangers, pushing old ladies out of your way and alternating between freezing outside and sweating through your 5 layers in overheated stores. Plus, you forgot where you parked.

It happened again: holiday shopping Scrooged you.

It doesn’t have to be this way.

Instead of letting the shopping experience kill your holiday joy, find unique experiences that make the process easy and fun. I promise; it’s possible.

Holidays on Oak Street, The Gold Coast

In Chicago’s exclusive Gold Coast neighborhood, the Oak Street shopping district has made efforts to lighten your load through free perks for shoppers.

To ease you in, they offer free valet parking every Tuesday between 10am and 2pm through December 18th (57 E. Oak St.). No more circling the block or the packed lot praying to the parking gods.

And just when you start dragging and daydreaming about your warm couch, Oak Street steps in with a complimentary Illy espresso. You can get yours every Saturday between 10am and 2pm at 57 E. Oak St.

If your schedule doesn’t allow you to take advantage of the afternoon offerings, do not fear. Many stores have extended hours during the busy buying season.

The best part? You never know when your generosity might pay dividends – with every $50 purchase at Oak Street boutiques and salons, you’re automatically entered into a prize raffle. Every Monday, they announce a winner (and no one will tell if you keep the prize for yourself).

One of a Kind Show at the Merchandise Mart
one of a kind show
Photo Credit

If handmade artisan goods are more your style, head to the Merchandise Mart between December 5th and 8th to browse unique gifts from over 600 artists under one roof.

No matter who is on your list (and how picky they are), you’ll find something that suits them. For your eccentric, fashion-obsessed sister, why not a necklace made of doll shoes? And a unique, masculine watch would be perfect for your hip, impossible-to-please boyfriend.

Tickets are only $12 per person. But, if you want to really make a fun day of it, they also offer the Friend’s Day Out package, which includes 2 tickets, 2 reusable shopping bags and 2 lunches at any of the show’s cafes.

If your list includes the folks that have it all, and if you don’t like shuffling from shop to shop, then this artistic shopping extravaganza is perfect.

Christkindlmarket, Daley Plaza
one of a kind show
Photo Credit

For those who like to combine their shopping with spiced wine-guzzling and bratwursts, the traditional German Christkindlmarket is the place to be.

If you’re up for braving the chilly temperatures, you can find unique gifts and a good time at this outdoor holiday festival that goes from November 26 all the way through Christmas Eve.

Started in 1996, the festive event was inspired by the nearly 500-year-old Nuremberg holiday celebration.It’s a favorite of many Chicagoans and visitors, who get to experience a distinctive, old-Europe tradition. And it’s certainly more fun than a food court and a department store.

In addition to the many food & drink vendors and gift stands, visitors can attend a wide variety of special events. There are several musical performances and numerous activities for children. And let’s be honest, isn’t everything better with gluhwein and sausage?

Every year it seems we have less and less time to simply enjoy ourselves during the holidays. What’s supposed to be a fun, relaxing time often ends up feeling like just more chores and work. Every January, you swear you’ll do it differently next year, right?

It’s time to put your holiday money where your mouth is. Instead of trudging through a crowded mall, choose one of these special events to get your shopping done while still remaining merry and bright.

For more information, visit

Post was contributed by Brian Burt

About UPchicago Team

Urban Philosophy is a way of thinking that you develop when you’re a true city person. Whether you’ve spent your whole life living in Manhattan, or you just moved from small-town Iowa to the city of Chicago, the longer you stay, the more you come to understand what it means to live in a city. Our Urban Philosophy is that no matter who you are, where you are from, and what your likes and dislikes may be, there’s something for everyone in city life.

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