Things to do in Chicago this Weekend in the Bustling Loop

It’s amazing how a little adjustment of routine can refresh your entire view on your home town. Towards the end of January, as the winter sets in and the glittering distractions of the holiday season have become a memory, it’s easy to fall into a slump. The cold wind blows down the shore, blasting through layers of fleece and wool. There’s no reason to look up, let alone go out and find things to do in Chicago.

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Enter Staycation Weekend in Chicago!

The last weekend of January, glum but not as typically cold as we’ve been having the last few years, we had the opportunity to dive into all that Chicago has to offer. We decided to focus on one of Chicago’s oldest neighborhoods, the Loop. Named after the circular path of the overhead elevated train lines (the El), and once primarily a business district, the Loop has shifted from a 9-5 office drone zone to a super dynamic 24-hour neighborhood.

So, here’s the thing. I kinda grew up in the Loop. My mom had a cafe that was open for the business crowd (6am – 5pm, generally) and the occasional weekend and evening (4th of July, Bears games). Growing up, it was a place to leave as fast as possible. Having grown up, I was delighted to discover all the amazing adventures the Loop has to offer during a weekend in Chicago.

Things to do in Chicago


We based our stay at the Hampton Inn Chicago Downtown, just off bustling Michigan Avenue on an almost-forgettable little stretch of Wacker Place. We took the El into the Loop and walked just a couple short blocks from the station, enjoying the Friday evening bustle of the commuting crowd, trains rumbling overhead, cars and busses zipping by. The Hampton Inn feels a world away from the bustle of the street just outside. Stepping in through unassuming doors, the soaring double height lobby takes you back in time.

Originally built in 1928 as the headquarters for the Motor Club, the 15-story art deco high rise was lauded by the Chicago Tribune as “a monument to the progress of motordom.” After years of gradual neglect, it was completely rehabbed in 2015 after standing abandoned for a decade. The remodel paid attention to authentic details: original metalwork, millwork and lighting graces the double height lobby.

A 1928 Model A Ford sits on a mezzanine balcony overlooking the lobby, while a full-wall mural shows the American highway routes of 1929, when the office building was originally opened. Anchored by Jack’s Bar, featuring local brews and specialty cocktails including “giggle water” (a curious mix of gin, spiced rum, bourbon, tonic water, simple syrup, lime juice and parsley), the lobby is known amongst local professionals as a great place to hang out after work.

Get the best rate at the Hampton Inn Chicago Downtown/N. Loop/ Michigan Avenue now! 

Things to do in Chicago this weekend


The rooms are comfortably appointed, with either a king or 2 queen beds. Some are ADA / mobility accessible with roll in showers, while others have bathtubs. Our room was in the -01 block on the northwest corner of the building. It took full advantage of a view slotted through high rises, straight up the Chicago River. Iconic drawbridges, city traffic, flags and pedestrians had my daughter captivated!

We quickly settled in and then set off to explore the Loop. First order of business: dinner!

Check the best rates and availability in Chicago now! 

Things to do in Chicago


We walked a few blocks to Revival Food Court, a recently opened food hall in another landmarked building, The National. Revival is a comfortable and spacious food hall outfitted by local Chicago craftsman Dan Sullivan. It features 15 fast-casual local small eateries, including Antique Taco, Brown Bag Seafood Company, Urban Slice Pizza. Most significantly for my daughter, it has Furious Spoon ramen.

We assembled a collection of ramen, ahi poke, and smoked brisket, as well as a few craft cocktails for the parents, and dug in. Lots of noodle slurps later, the music cranking, my daughter Avi expressed her full tummy bliss with a little dance jam in the middle of the hall, eliciting giggles and smiles from all.

things to do in Chicago


After that, we walked over to the Fine Arts Building to see Feathers of Fire: a shadow puppet show, part of the International Puppet Festival. A puppet festival? Moreover, a SHADOW puppet show? I had no real idea what to expect, but the preview was captivating and I had called to confirm that it was toddler friendly before buying tickets.

Walking into the Studebaker is an experience unto itself: built in 1898 as a vaudevillian theater, I used to go there with my mom in the 1990s to see foreign films. It was completely restored in 2005, and was one of a dozen city locations hosting more than 50 puppet shows from around the world.

Things to do in Chicago this weekend

Feathers of Fire was incredible: a Persian epic, told in cinematic shadow form, with elaborate translucent headdresses, great music and often hilarious lines. The show finished with an in-depth demonstration backstage, revealing 8 actors, more than 1060 cues and hundreds of props and puppets. Everyone in the theater was captivated. Avi was literally sitting on the edge of her seat, motionless for the entire 70 minutes of the show. My husband couldn’t stop raving about it for the rest of the weekend!

Thoroughly delighted with our Friday evening, we decided to head back up Michigan Avenue to the Hampton Inn Motor Club. Avi settled into her crib quickly, and we followed behind, delighting in a comfortable, quiet and plush sleep in our king size bed.

things to do in Chicago The Loop


Saturday morning, I woke to see Avi standing in her crib, gazing out the window. “Wook, mommy!” she said when she realized I was awake. “So many caws, and bwidges, and fwags! Wet’s go outside and see the city!”

How could you say no?

We popped down to the lobby for coffee and the fabulous Hampton Inn breakfast. The aroma of freshly made waffles, pork sausage, Denver omelets, and fresh coffee was too much to resist. Avi had a laugh at the to-go coffee cups – she kept saying “mow-stache, mow-stache!” and I realized we had smiley lips and mustaches on the cups. With a laugh, we set out to explore the city some more.

things to do in Chicago


Chicago has something for everyone, in all weather. A blowy snowy day just adds to the charm, so long as you are dressed for it! The Loop features every kind of entertainment. Pop into galleries and museums. Take in concerts and theater performances. The shopping on State Street, parks cafes and restaurants – it’s hard to pick what to do!

We started our morning at the Art Institute of Chicago, named the country’s best museum. The Modern Wing houses the Ryan Education Center. This is a great resource for families as it features a play area and hands-on art making activities. Kids also love the Thorne miniatures room, featuring painstakingly crafted miniature interior design vignettes; every visit yields something new.

We discovered a little trick to getting some museum longevity. We asked our 2-year-old to find doggies in paintings. Turns out there’s lots of dogs in the medieval, renaissance and impressionist galleries! After total art saturation, we bundled back up and into the urban grid for some lunch.

Things to do in Chicago


Once upon a time, dining in the Loop was essentially one of 2 options: quick take out for the office crowd or overpriced fancy dining for the hotel and theater crowd. I was delighted to find neither in Cochon Volant, a new brasserie at the corner of Clark and Madison, in the heart of everything. The humorous pig illustration on the windows gives way to an elegant French brasserie, with soaring ceilings, beautiful mosaic tile floors, Carrera tables and plush booths accented with antiqued mirror and an expansive wood bar.

The brunch menu is ripe with decadent options, from a duck confit omelet to a thick, fluffy stack of pancakes topped with blueberry compote. An entire bakery display showcasing flaky croissants, sprinkled donuts and delightful muffins. That this is actually a hotel restaurant, attached to a Hilton lobby, had me a bit surprised, but every moment was beautifully crafted and in fact I can’t wait to have the excuse to return!

hampton inn chicago downtown N Loop

Date Night in Chicago

After lunch, we transitioned to adult staycation time. After all, there are plenty of things to do in Chicago without kids. My daughter went to her grandmother’s for the rest of the afternoon. My husband and I prepped for an evening on the town.

In November, I had received a mysterious, wax-sealed invitation. The Committee of Twelve was graciously requesting my attendance at an invite-only masquerade ball. Intrigued, I accepted – and this evening was the night.

Twelfth Night, as the soiree is known, is one of Chicago’s oldest running parties, inviting bawdy and boisterous behavior in disguise at one of Chicago’s finest historic hotels. Dress code is masquerade black tie – a mask is mandatory – and prizes are given for a variety of categories. Glittered up as a mermaid, I was runner up best female costume!

Sometime far later than my usual bedtime, we walked back to our wonderful hotel, and sank into dreamless sleep. That may have been the best sleep of my parenting life – the noon checkout let us doze quite late…..following a lazy coffee in the beautiful lobby, reading a fer-real, print ink on the hands newspaper. We headed back to our own neighborhood, recharged and relaxed. We will definitely be back to the Hampton Inn for a future weekend “away!”

Under the Radar Chicago Summer Festivals And Events


Arts in the Dark started as a participatory Halloween parade, and this summer, expanded into summertime.

The Lantern Procession illuminates Chicago’s newest parkland, the Riverwalk in downtown Chicago. Dozens of Chicagoans celebrate their creativity by creating glowing lanterns; the procession winds its way along the promenade of the Riverwalk, attracting musicians, smiles and laughs along the way.

The best place to view is the River Theater, the stretch of riverwalk between Clark and LaSalle. The best WAY to enjoy the parade is to participate! The July 2018 theme was Starry Nights and Flying Creatures.

August 2018 is Chinese Valentine’s Day. Want to participate? Riverwalk participants meet at the jetty between Franklin and Wells at 7:30 pm if they want to walk with their lanterns in the parade.

The annual Arts in Dark parade happens about a week before Halloween ever year.

The Chicago Full Moon Jam

What started out as a small fire jam for a friend’s birthday has grown into one of Chicago’s most energizing monthly events. The Full Moon Jam brings together Chicago’s talented fire dancing community, drummers, and thousands of spectators.

Located south of Foster Beach, on the great lawn near the soccer fields, arrive early for prime spots and some pre-jam yoga. Spread a blanket and enjoy a picnic while fire breathers, hoopers and fan dancers welcome the night while the drummers drive the rhythm.

The fire usually lights by about 7:30pm and ends at 10pm. Be sure to stay for the amazing finale each night!

One note: this is on Chicago Park District land, and the closest bathroom is a long 12 minute walk – be mindful as it gets dark!


There are so many arts festivals in Chicago, but only one that encourages adventurers of all ages to participate in creating the installations themselves.

FIGMENT began as a one day event in New York City and has grown into a multi city, annual event. Participation is key. Dozens of installations throughout the park invite you to paint, dance, move, laugh and share joy. Create a mask, join the band, dance a dragon across the park.

Completely volunteer driven and participant focused, FIGMENT’s goal is to advance social and personal transformation through creativity, in the form of free participatory arts events and exhibitions.

Join the fun in July, or consider creating your own installation! Figment is 1pm-6pm in Mozart Park, and our friends from Pyrotechniq are usually spinning 6-8pm afterwards.

IgNiTe by Pyrotechniq Productions

The original fire production team in Chicago is breaking the mold AGAIN. Collaborating with Five Alarm Fireworks, IgNiTe: A Fireworks and Fire Dance Spectacle is pulling out all the stops. Fireworks choreographed with fire dancers will light up the night sky, delighting audiences of all ages at the iconic Garfield Park Conservatory.

Come early to enjoy the gardens, then spread your blankets and enjoy a picnic on the lawn. The event opens at 6pm, while the entertainment begins at 8:15pm. VIP tickets are available. Part of the proceeds help support the Chicago Fire Jam! 

Many thanks to the Hampton Inn for hosting my family for two nights. As always, my opinions are my own. When they aren’t you will be the first to know. Photos via

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3 thoughts on “Things to do in Chicago this Weekend in the Bustling Loop”

  1. Kristin @ Camels & Chocolate

    Would you believe I haven’t been to Chicago since the launch retreat for Travel Mindset?!? I think that was maybe four years ago now. Crazy! And it’s just a 45-minute CHEAP flight from Nashville, too.

    1. Keryn Means

      Well… if it makes you feel any better I haven’t been back since I graduated from grad school in 2006. I met Tai (the author and all around Chicago guru!) while working as an office manager back in 2004 in The Loop! I NEED to get back!

  2. Candace Glenney

    Chicago is one of my faves! Thanks for some great suggestions!

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