Long Layover Chicago

For our most recent trip to Mexico, we had a few options for how to get to the beautiful, vibrant town of Sayulita. Whichever option we chose, it was going to be a long journey from Hong Kong to Mexico. To break up the trip (read my tips for traveling with a newborn or traveling with a 6 month old), we decided to do a long layover in Chicago.

Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago

With less than 24 hours in the windy city, we were fortunate enough to have generous family let us stay with them during our quick visit. This layover guide is made for families who will be visiting Chicago with baby or kids in tow — i.e. it’s leisurely and not rushed. If you’re like us, you’ll be tired after flying with your little one and won’t want to pack 12 hours of hurried visits from site to site.

Instead, relax, soak up the city’s beautiful architecture, and make the most of a Chicago layover.

Long Layover Chicago

Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago

Transport

With limited time, make things easy on yourself and take Uber/Lyft/taxis to get around. We tried out Uber and taxis and found Uber to be cheaper. We hopped in one both from and to the airport.

What to Eat

Chicago’s deep dish pizza is an iconic choice and although I wasn’t expecting to, I loved it! But my recommendation here has to go to Frontera Grill. I know what you’re thinking, Pristine, you’re from Texas, you were on your way to Mexico, but your dining recommendation is for a Mexican restaurant in Chicago?!

Yes friends. This place is so damn good. I’ll admit we did not eat at the flagship restaurant, but we ate at the airport restaurant twice and Peter and I both loved it so much. Seriously. It’s that good.

Peter said they have the best bloody mary’s he’s ever had (and he tries them all around the world) and I can only imagine the wonders of the food and drinks at their full restaurant.

Frontera Grill
445 North Clark Street
Chicago, IL 60654-4682
(312) 661-1434

Layover Itinerary

First stop? A trip to the Chicago Athletic Association. Once an elite men’s club the hotel has since been renovated into a gorgeous hotel.

Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago

Chicago Athletic Association
12 S Michigan Ave

It’s worth a quick walk around itself to admire the beautiful gothic architecture, but on your way out, stop by Fairgrounds Coffee for a coffee from a selection of craft roasters or choose from a curated selection of teas. After a flight, and depending on the time of year you’re visiting Chicago, you’ll want a warm caffeine boost to put a little pep in your step during your quick visit.

Fairgrounds Millennium Park
Chicago Athletic Association Hotel
12 S. Michigan Avenue
(312) 448-9015

Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago

On this same street you’ll find a few of the usual chain options like Starbucks, Pret, Peet’s Coffee, and while I’ll admit I do head to Starbucks often in Hong Kong, when there’s a more unique and enticing option for a coffee, it’s a must try!

Since you’re just across the street, I think you know where we are headed next–

Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago

Cloud Gate
AT&T Plaza at Millennium Park

Now, it’s not just because I was traveling with an architect, but Peter and I enjoyed Cloud Gate so much. Even as a non-architect, I loved admiring the sculpture from each angle and the energy in the park at the sculpture was so vibrant and joyful. Everyone there was so happy and that added a lot to the experience.

Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago

Once you’ve had your fill at “The Bean”, you can either choose to keep exploring the park or head further into the cityscape. We made our way down to the Crown Fountain (no water during our visit as it was winter) and it was so bizarre/fun seeing two giant faces of Chicagoans looking back at us. Almost a thousand Chicagoans randomly appear on the two screens.

Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago

Afterwards, we strolled past shops and more skyscrapers towards the Chicago Riverwalk. 

Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago Long layover Chicago - Itinerary and tips for how to spend a long layover in Chicago, Illinois. Options for solo and family travel in Chicago

By this time we were pretty worn out after only a few hours of sleep, but Chicago is a beautiful city and this made me anxious to spend more time in the city exploring and enjoying it all. I think another (and much longer) trip needs to happen soon!