Weekend on Lola


One of the coolest perks we have at Lola is a monthly trip giveaway which we know as “Weekend on Lola”. At the beginning of each month, someone on the team wins an all-expenses paid weekend trip to a destination that our blog has featured. The winner travels to the destination, tries out a few handpicked restaurants and activities we’ve recommended, and stays at one of our featured hotels. The only catch? We have to take awesome pictures and put it all together in a blog.

Last month’s winner , Yofred (one of our product designers!), went to Chicago. Here’s where Yofred ate, saw, did, shopped, and slept. All in his own words of course.

How did you feel when you got picked for the Weekend on Lola trip?

I had gone out for coffee and as I was coming back into the office, everyone started clapping and chanting my name. At first I was confused, but when I found out I had won the “Weekend on Lola” for Chicago, I was really pumped. I was really excited to try out our handpicked recommendations.

Where did you stay?

The James and the Chicago Athletics Association.

What’s the first thing you do when you get to a hotel?

Drop my belongings off in my room and head down to the hotel bar for a whiskey drink. It’s a nice, relaxing way to take in my surroundings.

Did anything happen on the trip that Lola helped you with? Was there any Lola magic during the trip?

There certainly was. My return flight was delayed, and my travel agent reached out to me see if they could help with anything. She called my airline to figure out what was causing the delay. Even though there was nothing we could do about it, having someone along the way who was looking out for me made me feel more at ease on the trip.

Me at the beginning of the trip being super excited after arriving in Chi-town. I call this my “model pose”.

Shout out to The James hotel on East Ontario for comping a room in the heart of Chicago. The lox-laden breakfast in the hotel’s restaurant was delish.

For lunch, Lola guided us to Little Goat which was busy but lively. Chicago-based rapper, Common, was also there grabbing a bite to eat proving lending it some local cred. Sadly, we didn’t get a selfie with him.

The friendliness of the staff at Little Goat made me think that service out in the Midwest is a notch higher than Boston. The food was excellent and it made me want to try out everything on the menu. Caution: The food portions are super generous, so tasting everything on the menu is next to impossible.

If you’re in Chicago, a trip to Wrigley Field is a must! An Uber ride from Downtown made it very convenient to quickly get to north of the city where the park was. Here you can see the Cubs already kicking butt even in the third inning.

Built in 1914, you can feel the history at the second oldest baseball stadium. The grit and character that epitomize this place cannot be found in other stadiums. The excitement and camaraderie at the game was contagious.

The Cubs are finally good after nearly a century and the city is paying attention to its team again.

Food at North Pond, a Michelin star restaurant, was exactly what we had hoped- creative and daring. If you’re afraid of the dark, don’t go at night! The restaurant provides a dark and moody ambiance, but it wasn’t always clear what was on our dishes.

My favorite part of Chicago was seeing all the skyscrapers from legendary designers Mies van der Rohe, Raymond Hood, Fazlur Kahn, and others. We took a ferry tour called First Lady Cruises to experience the diversity of architectural styles. The tour took us from art nouveau to neo gothic to post-modern architecture. Super cool!

The Tribune Tower

The Trump Tower. You may not like the presidential candidate, but there’s no denying the tower itself is stunning. Also, Chicagoans know that this building replaced a rare but major eyesore on the riverfront.

Aqua (it was designed by this awesome female designer).

Stand at the base of Willis Tower to get a good perspective of just how tall these skyscrapers are.

It was immediately clear the heart of Chicago lay within the lakes and rivers that run through the city. You could see both locals and visitors hanging out around the water.

I took this photo while on a walk on Lake Michigan. The waterfront was so serene, and the walk was a nice reprieve from the chaos of the city. I highly recommend doing this if you have the time.

We loved staying at the Chicago Athletics Association (highly recommended!). This was once a men’s athletics club, and has now been converted into an upscale hotel. It overlooks Millennium Park and is in the ideal location to experience the city’s nightlife.

These old-school games at the hotel kept me busy while I was waiting for my Ubers. Great little way to kill time.

The rooms at the Chicago Athletic Association are the perfect blend of character and class. I was blown away by the thoughtfulness put into each detail of my accommodation. Check out this bathrobe. You can find subtle thematic odes to the hotel’s sporty history like this one.

“The Milk Room” inside the hotel is a coffeeshop that quietly becomes a speak-easy at night. This “cafe” is very popular and can only fit about a dozen so make sure you call ahead to reserve your seat.

If you’re looking for a gorgeous view of the park from your window, definitely book a room known as a “Millennium room” at the hotel.

My favorite perk of being a guest at the Athletics Association was being able to skip the long lines to enjoy drinks at the hotel’s rooftop bar Cindy’s. The view from up there is amazing. Tip: Don’t go up too late. After a certain time, they draw the blinds and you missed out on the beautiful view..

A whiskey drink (and a glass of water) at Cindy’s to unwind after a long day touring Chicago did the trick.

Check out the beautiful Jay Pritzker Pavilion in Millennium park. It’s a cool place just to lounge around in.

Eataly in downtown Chicago offers a variety of authentic Italian cuisine. Make sure to get there early as to avoid the massive crowds.

One of our nights out, we went to the comedy club The Second City. We were treated to some of the funniest comedians in the city after a long day of exploring. This is where the likes of Tina Fey, Stephen Colbert, Chris Farley, Amy Poehler, Steve Carell, and John Candy once took the stage.

From what we ate to what we saw, this trip was a homerun. The only downside I can think of is the fact that I ate way too much food. I’m coming back for you, Chicago.

A huge thank you to our wonderful travel agents who helped me out in many unexpected ways and guided my Weekend on Lola trip and made this amazing experience possible.

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