72 Hours in Chicago: The Perfect Weekend Getaway

December 1, 2018 by Ashlee & Crystal

72 Hours in Chicago: A Perfect Weekend Getaway

Chicago Theater Sign

It’s official! Our first trip to Chicago is in the books. We only had 72 hours to try and take in it all in, and let’s just say, it looks like several encores are in our future. A quintessential big American city, you could stay for weeks and still not experience all that the city has to offer. Thanks to the helpful insights we received from family, friends, and the infinitely bountiful world wide web, we came up with a fairly flexible wish list and a handful of must-dos.  In the interest of enjoyment and sanity, we wanted to allow plenty of time for situational improv and the occasional nap, so we were resigned to the fact that we probably wouldn’t hit them all (happy sigh). As happens frequently, this trip was not without a few unexpected snafus, but we embraced the experience and enjoyed every minute and can’t wait to go back! We’re excited to (finally) share the highlights with you.

The Chicago Tribune Tower
The Tribune

Baseball, Architecture and History

Chicago calls to mind images of the Chicago River, iconic skyscrapers, museums, theater, prohibition, Chicago dogs and deep dish pizza. And springtime means baseball. What better town to take in a ball game than Chicago? It just so happened the Cubs were playing at home the weekend we were there. For us, it was a no brainer. The theme of our first trip to the Windy City would be baseball, architecture, and history . We were told by several people who used to live in Chicago that late May is a great time to visit for weather. It was quite warm in the high 80s (even by Texas standards), but sunny and perfect for exploring on foot, by skyscraper, and by river.


For a reasonable price, we booked a room at the beautiful historic Palmer House Hilton located at 17 East Monroe Street.  We’ll start with what we liked: the location, the lobby and the rate. 

The Pros: The lobby, the location and the rate.

The location and price are excellent. We were within walking distance to the Chicago Theater, Millenium Park, the Art Institute of Chicago, the Chicago River, and the Red Line L. If you’re up for it, you could also walk to the other museums. To save time and energy, we opted for Uber when we visited the Field and the Shedd. The real draw here is the lobby. It’s stunning – the perfect place to enjoy high tea in the afternoon or a cocktail in the evening. The Potter’s Chicago Burger Bar serves up excellent burgers (we tried the Palmer Square and the Pilsen) and cheese curds. Legend has it that the brownie was invented at The Palmer House, so we couldn’t resist “the original brownie”, a delightful chocolate confection served with cherry and walnut ice cream. 

The Palmer House Brownie

The Cons: interior noise and temperature

As with many historic hotels, there are drawbacks to consider. The elevators were quite noisy until around 2:00am and our hotel room was warm and stuffy. Both of these issues could have been isolated to our particular location, but it’s an old hotel. We absolutely love historical buildings, but they’re  frequently lacking in modern conveniences. For us, it was worth the trade-off, but it might be a dealbreaker for others. Surprisingly, the water pressure was great for an old hotel. If you stay elsewhere, it’s definitely worth a visit for cocktails in the lobby. 

Day 1: Wrigley Magic and the iO Theater

Wrigley Field Home of Chicago Cubs
Storied Wrigley
Wrigley Field Interior
Play ball!
Ashlee & Crystal together at Wrigley Field
If you don't take a selfie, then it didn't really happen, right?

Cubs v. Giants 

The Draw: The second-oldest ballpark in the nation and the 7th inning stretch.

In an effort to make the most of our first day, we booked a 7:00am flight out of DFW hoping to make the opening pitch of an afternoon Cubs game. Unfortunately, our flight was delayed three hours putting a huge wrench in our itinerary right off the bat. We didn’t get to our seats (beer and peanuts in hand) until the start of the 5th inning! Lesson? Never underestimate the power of a plane with a mechanical problem, no fuel, and no flight plan! In hindsight, and even with an estimated arrival of 9:30am, we should not have scheduled an afternoon game for the day of our arrival. Better to leave this day open to a more flexible activity like a museum, exploring on foot, or casual dining. The good news is we got there in time to experience the magic that is Wrigley. There is something so uniquely American about snacking on peanuts and beer and singing “Take Me Out to the Ballgame” with 40,000 other baseball fans during the 7th inning stretch. As an added bonus, we stumbled into Al’s Beef after the game. A local chain, yes, but fantastic. We split the Italian Beef and a Chicago Dog – both delicious. Not sure we’ve had better French fries – seriously.



The Improvised Shakespeare Company at the iO Theater

The Draw: No trip to Chicago would be complete without comedy…wherefore art thou Shakespeare?

After taking the L back to the Loop, we checked into the hotel before heading to The Improvised Shakespeare Company at the iO Theater. This is seriously so funny. You don’t really have to be a fan of the late bard to enjoy this show. It is so clever, in fact, we found ourselves wondering how they pull it off as if at a magic show pondering the secret to the illusions. One word: Brilliant.

Day 2: Best-Pancakes-Ever, Cloud Gate, Art & Cocktails

Cloud Gate, Chicago

Wildberry Café  & Cloud Gate

The Draw: Heralded spot for pancakes close to Millenium Park            

After a good night’s rest, we departed our hotel around 8:00am and made our way to Wildberry Café. This place is extremely popular, and even with our early arrival, we had a 45 minute wait. Do not despair! They take your cell number and text you 5 minutes before your table is ready. Excellent! No stupid pager thing to walk around with. Free to explore, we set out to find the Bean. This mirrored marvel is actually called Cloud Gate and is so much fun to walk around and take pictures of. Before we knew it, it was time for breakfast. Be sure to order the Signature Berry Bliss pancakes, no syrup required. Best-pancakes-ever! The bacon wasn’t too shabby either.

Art Institute of Chicago

The Draw: The greatest impressionist collection outside of Paris. 

We finished breakfast just in time to walk through the gardens of the Art Institute of Chicago and line up before the museum opened at 10:30am. We spent about 4 hours exploring before we ran out of steam. The highlight for us was the Impressionist Collection. It is so extensive that we felt at times as though we were in a museum in Paris. If you grew up loving doll houses, the Thorne Miniature Rooms were a real treat, too.

Chicago Prohibition Tour

The Draw: Speakeasies, gangsters and plenty of Chicago lore.

Tired and hungry, we attempted to get into Lou Malnati’s for some Chicago Deep Dish. Even after 2:00pm the wait for lunch was over an hour and our tour started at 4:00pm, so we settled on a snack and a quick change.  We booked our tour through Chicago Prohibition Tours. After this one, we’ve come to the conclusion that group tours might not be our thing. The tour itself was okay. We started at the Green Door Tavern making 4 stops by bus along the way before driving past the infamous Holy Name Cathedral toward the end of the tour. While in transit, the tour guide told stories of the Chicago mobsters. We tarried in each location long enough to hear a little back story about the speakeasy and have a drink and the occasional appetizer with fellow tour goers. Many of the buildings have been repurposed, remodeled, etc., so we didn’t see anything that any other bar patron couldn’t see. If we could do it again, we’d do some research into the Chicago mob and visit locations of interest independently. Maybe even get a story or two out of the bartenders while we’re at it. 

The Aviary

The Draw: Cocktails that look like they belong in a museum of art.

After reading the reviews and seeing photographs of cocktails that look like art, we had really high hopes for The Aviary. For starters, we had at least 4 people attending to our table. Only one was friendly. With such an extensive and exotic menu, one would think answering questions and making recommendations would be the rule and not the exception, but that’s not the vibe we got. The cocktails are definitely instagram worthy. Most looked better than they tasted. The appetizers that accompanied the flight left a lot to be desired. If we never have to eat fancified pork rinds again, we’ll be doing alright. We’ve come to the conclusion that there’s something to be said for simple, classic cocktails that don’t break the bank. Here’s looking at you, French 75. It might be worth a stop in for a drink and a photo op, but we’d skip the tasting menu. In the end, it felt pretentious and it took way too long.  The plan was to head to Au Cheval after for a late night snack of burgers and chilaquiles. Long story short, we didn’t finish in time. Oh well, add it to the list for next time. 

The Jungle Bird Cocktail at The Aviary Chicago
Cocktails at The Aviary Chicago

Day 3: Man-eating Lions, Cake in a Shake, and Dinner on Top of the World

Lake Michigan Coastline by day
Chicago by Day
Chicago Skyline at Dusk
View from the Signature Room by Night

The Field Museum

The Draw: A boy (or girl) named Sue and the Tsavo Lions

Hard lesson learned here; well, at least for one of us. Don’t drink all afternoon on a prohibition tour, skip dinner, AND have a fancy cocktail flight accompanied by pork rinds. The results are not good. We finally got going around noon and started with a trip to the beautifully impressive Field Museum. You could spend a whole weekend here easily. As soon as you enter the Classical Revival monument of a building, you feel as if you are in a large treasure chest. This museum has it all: animals (stuffed), dinosaurs (fossilized), and mummies (without curses) amongst a plethora of the world’s treasures and curiosities. Don’t miss the Tsavo Lions. The story of these infamous man eaters was made into a movie: The Ghost and the Darkness. Also featured: Sue. The largest most intact Tyrannosaur ever excavated. Go ahead – get lost!



The Draw: Chocolate Cake Shake

If you like chocolate and ice cream, nothing will beat the heat and satisfy a sweet tooth quite like the Chocolate Cake Shake from Portillo’s, an Illinois-based chain that has been serving up hot dogs since 1963. These days, the menu is huge. You’ll find everything from burgers, dogs and fries to ribs and pasta. We can’t comment on the food. We only went for the sweet stuff. A meal in itself, a slice of chocolate cake is blended into a milkshake. The best part is the gooey, ice cream drenched cake left at the bottom of your cup when you’ve slurped up your last bit of shake. Grab a spoon and  enjoy! 

The Signature Room

The Draw: A room with a view

Probably the best piece of advice we read before our trip: skip the Willis Tower and have a cocktail at the Signature Room instead. We took it a step further and enjoyed dinner with an incredible view from the 95th floor of the John Hancock Building. Dinner reservations just before dusk afforded us both day and night views of the skyline. As an added bonus, it saved us a trip to the Skydeck at Willis Tower. We started with an order of Shrimp Dejonghe and Lobster Bisque. For the main course, we both opted for Filet of Beef adorned with king crab and garlic herb butter complete with a side of Truffle Au Gratin Potatoes. For dessert, a blackberry and lemon cheesecake and due cappucini. The evening was absolutely perfect! The staff was so attentive that they were even kind enough to personalize our dessert. The lounge area on the floor above us was quite crowded. We suggest just splurging and having dinner. We had plenty of room, were never rushed, and there wasn’t a bad view in the house.

A beautiful dessert at The Signature Room
We never met a lemon dessert we didn't like!

Day 4: Architecture River Cruise and Shedd Aquarium

Architecture Cruise

The Draw: A history of the skyscraper on the Chicago River. 

We began our final day in the birthplace of the skyscraper with history and architecture on the Chicago River. From buildings in the Art Deco and Gothic Revival styles to Mid-Century Modernism and Post Modern, a Chicago architecture tour is truly a first-hand look at the evolution of the skyscraper. The Tribune Tower was our favorite. The Chicago Architecture Foundation is highly recommended for both walking tours and boat cruises. Due to time constraints, we chose the Shoreline Architecture and Sightseeing Cruise since it’s a little shorter in duration and also highly rated. In the end, 75 minutes was just right. 

View from the Chicago River Cruise

The Shedd

The Draw: Because aquariums are just really cool!

Our last stop before checking out and heading to the airport was The Shedd Aquarium. The Beaux Arts structure itself is something to behold and the aquarium is a great way to leisurely spend a couple of hours. We also really liked the fact that the aquarium was easy to navigate. It’s possible to pick and choose what you would like to see and when you would like to see it. So many aquariums and museums seem to have a maze-like setup in that once you start viewing a certain area or attraction, it’s not so easy to switch gears or skip the parts you don’t want to see. Not so with this one. Also, unlike the Field and the ARTIC, you can easily see everything in a few hours without feeling rushed. We do recommend, however, springing for the Chicago CityPASS if you plan to visit several of the museums. It will not only save you a few dollars on admissions but we also saved time with express admission.

Recycled Penguin at The Shedd Aquarium
Recycled Penguin

Our first time in the Second City definitely left us wanting seconds! We’d love to hear from our readers. Please drop us a line and tell us about your adventures in Chicago. In the meantime, cheers to Chicago!