16 Hours in Chicago

16 Hours in Chicago

Of all the amazing places I’ve been blessed to visit in America, I find Chicago to be my favorite spot. The people are so kind, the food scene is on point, there is so much to do and see and it’s easy to get to whether you are traveling from the north, south, east or west.

As a semi-frequent business traveler, I’m always looking for a chance to check out a few things that I wouldn’t get to see at home. I know that many of our wine club members are also travelers – both business and pleasure – and we all find ourselves in the same conundrum…what should I do and see with the limited time I have? Well, good news folks, I’m here to help!

Without further ado, I’d like to talk about my favorite city in the US – good ol’ Chicago! If you’ve never been, I highly recommend finding your way there sooner than later. Unless of course, the “sooner” would fall into a winter month, and then I recommend you wait until “later” (i.e. May – August seem to be ideal as far as this California girl is concerned). Below are some tips on where to eat, drink, be merry and rest your head.


Sofitel Chicago Magnificent Mile – This beautiful, modern property is in close proximity to the shopping and great restaurants of Michigan Avenue. Some rooms boast great views of the Lake Michigan and Willis Tower, while others feature expansive city and river views. But let’s be real, the draw here is “Le Bar” for some after-hours libations. They have an awesome selection of wines by the glass and flight, but their cocktails and complimentary bar snacks are killer!

Chicago Premier Suites – If you are lucky enough to be in town for more than a few nights, check out Chicago Premier Suites. They will hook you up with some of the finest high-rise apartment rentals in the area.

Whitehall Hotel – Nestled just off Michigan Avenue, this property has all the charm and mystery you’d expect from a bygone era.  Plus, David Letterman is known to frequent the bar downstairs for a late-night cocktails.  The rooms are quaint and affordable, and if being in the action is important to you, this is the perfect location.

Palmer House Hilton – Another historic property, this one located along the fringe of Millennium Park, they say this is where the brownie was invented. Yes, THAT brownie.  Created at the direction of Bertha Palmer ahead of the Columbian Exposition World Fair in 1893, this delectable piece of history, made from the original recipe, is still available here. The rooms are well-appointed and affordable, with fantastic views of the park and Lake Michigan, plus it has easy access to the “L” train.


Wrigley Field – Whether it’s baseball season or not, head into Wrigleyville. Find a bar stool to prop yourself on for a local Goose Island beer (I like going to Sheffield’s), then meander down to the field. If there is a game, you are in luck – although the tickets to see the 2016 World Champs will cost you! – but even if there isn’t, go for a ballpark tour.  I’m not huge into sports, but I do appreciate history and there is a ton of it here.

Chicago Architecture Foundation River Cruise – Climb aboard ‘Chicago’s First Lady’ for a very informative peek into the storied tales of the city and its astounding architecture. I have been to Chicago seven times and I’ve been on this cruise five of those times. It’s worth every single penny, every single time, rain or shine! I promise.

Millennium Park – With just a little time to kill, take a stroll around Millennium Park. If you are there in the spring, you will see all of the wonderful tulips in bloom, but no matter when you are there, be sure to grab a Chicago dog and find a comfy park bench for a seat and take it all in. Time commitment:
5 minutes to 2 hours +

Museums – The cultural scene is Chicago is robust. From the Shedd Aquarium and the Field Museum to the Art Institute and Museum of Contemporary Art, there is so much to do and see. I highly recommend using one afternoon to see one of these gems. Time commitment: 2 hours +


Blackbird – Acclaimed Chef Paul Kahan and his fabulous restaurants have been recognized with multiple James Beard Foundation awards. For a truly superb and special dining experience, give Blackbird a try. If you can’t get in, fear not! There are several other wonderful restaurants in the One Off Hospitality Group portfolio, including Avec, Publican, Big Star and Nico Osteria.

Monteverde – For pasta lovers, do not miss Monteverde – they literally have a live pasta theater! One of my members tipped me off to this spot  and I am so glad we made the $20 Uber trek to get there.  Not only was this one of the most delicious meals on our trip to Chicago last August, this was, by far, our least expensive meal as well. We ate our faces off but when the check came, it was a stunning $97. Do it!

Seven Lions – California transplant Alpana Singh and her team have created a truly elegant but accessible dining journey here. The food is outstanding and the opulence of the space itself certainly lends to the experience. Best of all, it is directly located off Millennium Park so you can stop in either before or after that walk I told you to take above! If you can’t get into Seven Lions or don’t quite make it to the neighborhood, try her other spots, The Boarding House, or Terra & Vine up in Evanston near Northwestern.


LondonHouse – Head up to the rooftop at the LondonHouse Hotel. You do not have to be staying on the property to enjoy their incredible upstairs bar. Be prepared for a lengthy wait for the elevator and a slow ride up after that, but once you get there, oh man is it worth it! We had the good fortune to watch practice runs for the Chicago Air & Water Show from that vantage point which was quite a treat. Although the website would have you think you need a reservation, we were told by a local wine club member we could just show up and I am so glad we did!

The Green Mill – Recommended to me by Dave Miner himself, transport back in time and enter The Green Mill, a traditional jazz club and cocktail lounge. Open until the wee hours of the morning, you can make time to come here after your dinner plans. There is live music every night of the week and the cover is a nominal $15 on a weekend evening, which is even less expensive during the week. No reservations are taken and tables are first come, first served. Keep that in mind because this place is always packed!

The Aviary – Sister to restaurants Alinea, Roister and The Office, The Aviary is “where cocktails and service are given the same attention to detail as a four-star restaurant.” Visionary chef Grant Achatz opened this hip spot in Fulton Market some years back and it is as hot as ever. Bring deep pockets; The Aviary isn’t cheap!

Dublin Bar & Grill – For something truly low key, head over to this daytime diner/late-night pub. A cool locals spot with very good food, this is a great place to grab beers and meet some new friends.  It’s close proximity to hotels and popular restaurant spots make this an easy choice.

Looking for other great tips? I’ve got more! Plenty more! Email me at laila@minerwines.com for tips on a fun, delicious journey!

Laila Subaie

Laila grew up in Sonoma county eating dinner out every night. Really. When your father is the owner and chef at a busy French restaurant, family time requires you to dine on fabulous cuisine daily. Her father’s motto is “teach them young”, and so at an early age Laila learned all about hard work, hospitality, food and wine.

In 2004, Laila entered the wine industry and has since gained invaluable experience, developed countless programs and is recognized as one of the leaders in her field.

Her creativity and passion for an unforgettable club experience, starting at the tasting room level and resonating through all points of contact, keeps her members interested and engaged.

When asked what’s the best part of her job, Laila says, “That’s easy, I get to interact with some of Miner’s most enthusiastic fans.” Sweet gig.


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