
The map for our Historic Chicago pub crawl
Downtown Chicago is overflowing with classic architecture and a history of high and low culture. Early skyscrapers graciously step up and back as they rise to better allow natural light to reach the street and pedestrians below. It’s just one of the architectural refinements that would’ve escaped me entirely if it weren’t for the Historic Chicago Walking Bar Tour and pub crawl. The promise of insights into architecture, local history, great drinks and company lured my travel buddy and me out on a vibrant Friday night. Over two hours we dipped into hidden lobbies, studied classic facades, historic photos on iPads and explored an underground watering hole. The tour began in the
Argo Tea Cafe on Randlolph Avenue, an easy walk from our hotel, the
Hyatt Centric on the Loop.

Lobby sitting area inside the Hyatt Centric the Loop

Hyatt Centric the Loop rooftop bar with views to the lake.
Given the mild spring weather it was a pleasure to cross the river, enjoying beds of tulips scattered across wide avenues and stop to sip draft Kombucha at
the Argo Tea Cafe. The registration fee covered the basics and tip cash was collected at the outset. After that we simply had to follow the leader, Elizabeth. She spoke quickly and began by engaging us in creative guessing games, then expertly herded us over the 3/4 mile walk. The veil of time was pulled aside with every anecdote, as she pointed out a sconce, bricked over window, elaborate carvings and so much more.

The clock inside the historic newspaper building of the Chicago Tribune.
Through a doorway at the back of the tea shop we stepped into the historic
Tribune Newspaper lobby. The towering skyscraper stands as a shrine to news, to a grander era with chandeliers, arched windows and a coffered ceiling that made us hush in respect. The walls and floor were inscribed with quotes with more than 120 stones embedded inside and out from important locations around the world. Most unusual was the tall, muted world map behind the desk. The layout was vertical and pale; mountains and continents stood in relief. Shredded dollar bills had been pulped and molded to create the three dimensional relief!
Out we went to the corner where the Shriners had built their Medinah temple just before the Stock Market crash in 1929. Carved with exotic reliefs with Abyssinian figures and winged embellishments drawn from Islamic designs, the building is topped by a burnished gold dome. Originally, the story goes, it was part of a dirigible docking station before the Hindenberg disaster turned those plans to ash.

Entrance to the subterranean, Billy Goat Tavern, immortalized in a SNL skit.
The city is no stranger to ashes. The great Fire of Chicago in 1871 devastated nearly 4 miles of downtown. It created a new slate for the captains of industry to erect a more ideal metropolis. They created an underground where trash and delivery systems still keep truck traffic off the upper downtown streets. Downstairs, just a block from the Tribune building, stood a corner bar,
The Billy Goat Tavern, immortalized by an early Saturday Night Live skit. We saw the ‘Wise Guys Corner,’ where early newspaper men and women spent long hours listening and drinking. The Goat is home to single/double/triple burgers and local brews. Our samples were served at an alcove table surrounded by framed photos of the original Billy Goat Siannis and his mascot side by side with media giants, sports figures and celebrities.

Sharing a snack on our pub crawl with Detours Chicago
Those were just a few of the stops covered in the Historic Chicago Walking Bar Tour. As it drew to a close, we passed the flagship Dylan’s Candy Bar. Cocktails in candy hues, garnished with gummy bears and sprinkles were on the bar menu (for those over 21.) The rest of the multi-level shop was a play land full of teens and young families, topping their evening with sweet confections of all kinds.

The flagship store of Dylan’s Candy Bar

Tiffany’s Peacock Doors inside the Palmer House Hilton Hotel.
After our pub crawl tour goodbyes we chose a different dessert, a late night brownie, in the hotel where they had been invented. The
Palmer House stands proudly full of marbled columns, a cavernous central courtyard. The street lobby once once housed C.D. Peacock Jewelers. When the hotel was rebuilt after the great fire, the jewelers drew the elite in through gilded Peacock doors created by Louis Comfort Tiffany. Inside the lofty hotel lobby several bars were in full flow for the Friday crowd. We chose a quiet booth in the restaurant and enjoyed plates of grilled octopus and vegetables before indulging in a brownie, created from the original recipe. (I’d recommend eating in the bar where it’s a bit noisier but there are better prices.)

Stepping into the Palmer hotel lobby

Brownie created from the original, first ever Palmer Hotel recipe.
Bertha Palmer, the original owner’s wife, was a savvy business woman and patron of the arts. She ensured that the City’s elite visited the hotel often. The story goes that, for a picnic box lunch with her society swells, Bertha asked the hotel chef to create a dessert that was less messy than sliced cake. The Brownie was born. Nearly a century later we were served a round Brownie made from the same recipe. It sat on a bed of chocolate syrup sprinkled with chips, nuts and cookie crumbles. My verdict? The round brownie was light, and more milk chocolate than the dark full flavor that modern brownies provide. It’s just a matter of taste, I like high cacao content chocolate, still not a crumb went to waste.
It was getting late but the night weather was mild and the street pleasantly peopled. Full of new facts about architecture, full of delicious food and drink, the walk back to our room at the Hyatt Centric Loop was the perfect night cap.

View across the river after our pub crawl. Yes, that’s one of Donald Trump’s towers.
Disclosure: Chicago Detours offers many architectural walking tours around Chicago. We loved the
Historic Chicago Walking Bar Tour and look forward to returning to sample more of their trips. We also thank the Hyatt Centric the Loop for our media rate.
Our pub crawl was complementary but all opinions are mine. If you go on a historic pub crawl
DeTours Historic Walking Tours. The historic pub crawl was our choice but there are many tours to select from. It was great mixing speakeasy ambiance, meeting locals and out-of-towners, plus the tickle of learning while tippling! Detours Historic Chicago Walking Bar Tour.
Hyatt Centric the Loop: Just steps from downtown attractions, restaurants, the high rail, it’s a new concept in hotel luxury. The lobby is modest but there’s an upstairs lounge, the Corner, with a snack bar, espresso machine, several rooms for dining and meetings. Our room was plush but modest – we had all we needed, enough space, lots of well placed outlets and great WiFi. The staff was courteous, thoughtful and my only regret was arriving a few days before they opened the rooftop bar in the evenings. It’s a perfect perch for a mild evening.
The Hyatt Centric the Loop.
Palmer House Hilton Hotel
There are so many historic hotels to enjoy in the downtown Chicago Loop that it’s hard to focus on just one. For this foodie, when I heard that the
Palmer House was the origin of brownies and that they were still baking the original recipe, the chance for a time travel tasting was too good to pass up. (Plus the elegant Palmer was less than two blocks from our hotel.)
Hope you enjoyed this post and get a chance to explore Chicago.
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Chicago is all time a pleasant place for me to wander, from the architecture to the food all is simply wow.
Loved that loop roof top bar.
It’s not as varied architecturally as Singapore because of Midwestern winters, I imagine, but there’s so much to see and do, it’s worth visiting again and again.
This sounds like a great way to explore the nightlife a bit more. The historic element adds something to a pub crawl. I’m usually there for a good gin cocktail! I like that they make the brownie to the original recipe and I wish other places would follow. I’d like to try this kind of tour. It seems like fun
Thanks for stopping by, Kate. The brownie was great and I definitely need to investigate more gin cocktails.
In Delhi we call it walks or hopping. Loved the word crawl. Such organized crawl is good way to enjoy and explore city.
Great post. Thanks putting efforts and writing this informative post.
You’re welcome, Himanshu. I’m glad you enjoyed the post. Will have to check out your Delhi bar walks or hopping one day.
I am super jealous of your historic pub crawl!
I haven’t been to Chicago in several years, but next time I go, I’m definitely going to do this!
In San Francisco, I frequent “The Hotel Utah Saloon,” which is the cities 2nd oldest bar, build just before the early 1900’s earthquake, such cool history!
I’m going to SF in August and will definitely check out the Hotel Utah Saloon. Thanks for the tip and I hope you get over to Chicago before long. Salud!
I love brownies and this one looks mighty delicious 🙂 Looks like a great line up for a pub crawl, lots to see and do!
I imagine you’d enjoy the night’s outing, Samiya.
A historical pub crawl sounds so much fancier than just saying that you are going on a regular pub crawl. Fancy drinking at it’s best! Haha. Great pictures and that brownie looks amazing.
Oh yes, I was there for the history…! Truly a great combination.
Lov these types of walks and yes Chicago architecture is amazing. I did a food walkign tout there too. I would have loved to have done a pub crawl and I want to try draft Kombucha now lol. Wow on that brownie!
Kombucha is a new favorite for me. It’s refreshing and there’s some pretty creative flavors out there now. Hope you return to Chicago one day.
Oh my. What an epic lineup and exciting day. I’m not a huge brownie fan (or chocolate anything fan for that matter), but I’m certainly a fan of anything booz related, and it appears you chose the more Speakeasy style of tour which would have been exactly what I would have done. Also, props for trying a bit of white wine on your tour! I’ll definitely be reverting back here next time I can make it to Chi-town!
Greig
Nice to hear you’ll be in Chitown before long. Do check out the pub crawl. Interesting company too.
i keep hearing what a great city Chicago is for architecture. So i can how a walking tour would be great. And I like the idea of drinks thrown in to the deal, gives your feet a rest!
Definitely glad I wore good walking shoes. They took great care of our group on the tour.
I love a good walking tour! The clock is so cool and I’ve always wanted to visit Dylan’s. That brownie looks incredible also! Great post.
Dylan’s was such a tickle. One of the locals on our tour told me to stop in. It was right near the end point of the tour.
That brownie is looking quite fantastic! Nice to hear a little history about it too. A good ole city tour ending it with a scrumptious dessert like that, sign me up please!
The tour didn’t include the brownie but I knew the Palmer was on our route home. Not hard to make an excuse to eat brownies any time of day!!
This looks like a great walking tour with something for everyone! The views from the Hyatt are incredible – I could spend a whole day drinking wine and staring out in the distance – and to top it off with a Brownie – Bliss!
That rooftop bar is stunning. Open seasonally it’s a perfect perch for happy hour hanging out with friends.
That is surely one of the most prettily presented brownies I’ve ever seen. Those peacock doors are stunning as well! Definitely a pub crawl I would be more than happy to attend 🙂
It was tasty and the doors were a surprise. I hope you get a chance to see for yourself.
That rooftop view is amazing. I’m heading to Chicago tomorrow, making note of your suggestions. That brownie you featured looks so good!
Hope you have a great trip, Sara. It should be a stunning time to be in Chicago.
Interesting experience, Elaine. It would have never crossed my mind to take a Walking Bar Tour when I was in Chicago, but after reading about your fun day I’d love to try it. However, the late night brownie at the Palmer House sounds more appealing to me. If it’s dessert, you can count me in.
You’d enjoy the tour, Anda. Not too long, strenuous and full of interesting facts, tastes and sweet company. Lots to discover in Chicago.
Sounds like a great tour (and those sweets- nomnomnom!). Chi-town is high on my list, I’ve gotta get there soon from the looks of it!
You’d love the incredible food options throughout the city.
I’ve never been to Chicago – every time I’ve gone to the States I’ve not been able to go for one reason or another. I’ve wanted to for a long time though. I’ll keep this tour in mind. That brownie looks amazing!
I hope you get the chance one day, Eileen.
This tour sounds fantastic. Just the type of experience I like to have in a new city. Chicago is calling me. I know so many great people from there and the food culture looks amazing #wkendtravelinspiration
Thanks, Katy. It’s a noble city. Sadly negative press is keeping some from visiting. There are always things to fix in big cities.
Elaine,
This sounds like a tour I would love. I love learning about the history and architecture of an area. I’m from IL near St Louis and have only visited Chicago twice with limited sightseeing. I definitely want to do this tour when I visit again. My mouth was watering at the brownie. Trying classic recipes just puts you back in that time. It looks fantastic! Thank you Bertha Palmer!! 😉 Thanks for sharing!
Yes! Thanks, Bertha Palmer. I’ll bet she never envisioned this long lasting legacy.
We’ve been in Chicago a couple of years ago. We should have done a Historic Walking Tour. There is so much we missed to see.
It’s a big city so there’s no way to do it all. I hope you can wrangle a return trip one day.
Love the concept of walking tours, especially when they get combined with local drafts and food speaking a lot about the previous past. Chicago will be happening for us pretty soon and we’ll keep Detours Chicago on our mind. Cheers!
Nice to hear you’ll be visiting Chicago soon. I hope you get a chance to take one of the walking tours.
You had me at pub. I love checking out walking tours in a new city, especially if they offer the chance to imbibe along the way. So many pubs. So little time.
Perfect place for a man on the lam.
I did not know the brownie came from Chicago! Just one more reason to go sooner rather than later!
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Thanks for joining the Weekly Postcard, Lolo.
It’s brownie time any hour in my book. Chicago is full of great eats and sips.
I did not know that info about the beginnings of the brownie! There are some amazing things to see when you walk around in a place, this looked like an interesting tour.
Great tour, small group, fun places and entertaining, professional leader. I’d do another tour with them again in a heartbeat.
I like your photos of the clock inside the Tribune lobby and the Peacock doors. There is so much architecture to investigate in Chicago.
Sounds like you favor the luxurious, historical details. I do too but old and new delight me when they’re well done. The Tribune Tower lobby is full of details you’d enjoy.
Pub crawls are always my favorite tours. You get so much of the colorful history of a city. Great article Elaine! #wkendtravelinspiration
So appreciate that, Jim. I’m new to the pub crawl scene but mixed with a little history, thoroughly enjoyed myself. Now who’s the designated driver?!
How I miss Chicago, simply put it’s my favorite city in the U.S the food scene is amazing as is the nightlife and Shedd Aquarium! The Palmer Hotel looks gorgeous and great pics of Chicago!
I so appreciate the kudos, Prateek. Lots more to see there and I’ve yet to make it to the Shedd Aquarium. Thanks.
We both love walking tours and while I often research my own small group tours can also be a great option and allow you to find things that we wouldn’t on our own. That loop roof top bar looks great.
Thanks, Toni. I do my own ‘tours’ too but sometimes in a new place it’s relaxing and fun to hand the reins over and just be present.
I love going to Chicago as I feel like there is always another place or site for me to explore whenever I go. From the architecture to the food, it really is a must see destination. Now I must add pub crawl to my next must-do when in town.
I hope you do return again and again, Christina.
I love walking tours in historic parts of cities. This Chicago tour of historic architecture combined with a pub crawl sounds right up my alley. The brownie after looks divine. The ceiling of the Palmer Hotel lobby is pretty impressive. I’d be tempted to lay down on the floor to take it all in (and to get a few photos that way).
That would be something, Donna, to see you taking pictures of the ceiling while on your back in the middle of the lobby! It’s a truly beautiful space on so many fronts. I hope you get a chance to see and sip soon.