Alex and I recently went to Chicago together for the first time earlier this month. My parents are both from Chicago and much of my extended family still lives there. Also, having graduated from a university in the midwest, many of my college friends now live in Chicago. Between my family and friends, I have been to Chicago countless times and I love it. I was so excited to share my love of the city with Alex. Even though I have been there many times, I typically don’t get to “play the tourist”, so it was really fun to do some sightseeing on this trip! Our Chicago visit was also a trip to visit my best friend and pledge daughter in my sorority, Emily. Emily is from the suburbs of Chicago and has worked in the city since we graduated college. I hadn’t been to see her in a few years, so I was well overdue for a visit and it was so wonderful to spend a few days with her. Emily was generous enough to let us stay in her beautiful downtown apartment. I have always loved her apartment; it has gorgeous views of Lake Michigan and the skyline. Because of that, I do not have any hotel recommendations for Chicago as of this post, but I do have plenty of recommendations for restaurants, bars, and things to do!

In case you want to see our itinerary, here is an abbreviated version:

Day 1, Friday: Cubs game and Wrigley bars, drinks at Signature Lounge, dinner at Farmhouse Chicago, frozen custard at Portillo’s

Day 2, Saturday: Walk through Farmer’s Market and Lincoln Park Zoo, walk along Lake Michigan to the Bean, lunch at Xoco, party at friend’s downtown condo, Wells Street Art Festival, watch Blackhawks game at Old Town Pour House

Day 3, Sunday: Brunch at Kanela, walk down State Street to see beautiful homes and former Playboy Mansion, browse in State Street shops, drinks on the rooftop at J. Parker, dinner at Trattoria Roma

Day 4, Monday: Walk around Navy Pier, have lunch at Haray Caray’s Tavern, get popcorn at Garrett popcorn, ride the ferris wheel, tour Revolution Brewery, dinner at Adobo Grill, comedy show at Second City

Day 5, Tuesday: Architecture Boat Tour, lunch at Gino’s East, head back to the airport

Now, for my recommendations…

RESTAURANTS:

One of the first stops on our agenda was to Signature Lounge on the 96th floor of the John Hancock. There is also a restaurant called the Signature Room on the 95th, but as you might expect, it is quite pricey. We opted to stick to a drink at the Lounge. There was a bit of a line to get on the elevator, to get a seat in the Lounge, and to take the elevator back down, but in all we probably waited 15 minutes and it was well worth it to see the sunset over the amazing Chicago skyline. We stayed long enough to see the skyline sparkle with lights at night. (Insider’s tip: It is $18 to go to the Hancock Observation Deck, but about $15 for a drink at the Lounge (view included!). If you want a cocktail to accompany your visit, go to the Lounge!)

Our first night in Chicago, Alex, Emily, and I had planned on eating at The Purple Pig. Unfortunately, even though we arrived at 10pm on a Friday night, there was still a 2 hour wait, which none of us could handle. Emily consulted her trusty OpenTable app and found a 10:15 reservation at Farmhouse Chicago, so we gratefully took it and hailed a taxi. Farmhouse Chicago was adorable. It is a farm-to-table concept with local ingredients and their bar has a wonderful selection of local craft beers. Alex got to try cheese curds for this first time (he hasn’t spent enough time in the Midwest, clearly) and we all enjoyed our meals. Farmhouse Chicago is a must if you enjoy trying local fare with a twist.

After dinner, Emily headed home to rest after a long week of work, while Alex and I stayed to walk around the city before calling it a night. We stopped at Portillo’s, one of my favorite Chicago “fast-food” stops. I love Portillo’s Italian beefs and Chicago dogs. Since we were so full from eating at Farmhouse Chicago, we settled on sharing a frozen custard sundae, which was delicious. Chicago has innumerable great restaurants and plenty of great places to get typical Chicago fare, but Portillo’s is consistent and located conveniently close to wherever you are. And if you love it, but don’t live in Chicago full-time, you can mail-order it to your home. Can’t beat that!

On Saturday we went to lunch at Lunch at Xoco after walking through the Zoo, by the Lake, and to the Bean. Xoco is owned by Rick Bayless, who also owns Topolo and Frontera. We each got different Tortas (sandwiches) and were all very impressed with our choices. I picked the Pepito and I think we all agreed that mine was a clear winner. The short ribs were tender and paired perfectly with the accompanying sauce. Alex got the Ahogada which came with a delicious tomato broth and Emily chose the chicken.

Sunday morning, we all got lunch at Kanela, a cute little breakfast cafe with a couple of locations in Chicago. We went to the newest one in Old Town as it was only a few blocks from Emily’s. Breakfast was delicious and we all enjoyed our meals. A must is the monkey bread. Alex and I split it and it was to die for. My main meal was the Strawberry Waffle. If you like strawberries, this waffle is for you: A waffle with strawberry preserves and fresh strawberries, topped with a sweet creme fraiche. Perfect! Everything on the menu looked and sounded amazing, so I don’t think you can go wrong with anything you order.

For dinner Sunday, we went to  Trattoria Roma, in Old Town. It is a very popular restaurant and for good reason. The meals are both delicious and filling, reminding me of authentic Italian restaurants in Italy. They also served sangria, which I think we all really enjoyed.

On our last night, we had dinner at Adobo Grill Old Town. It was fantastic! They made guacamole tableside and I don’t think we saw anyone in the entire restaurant without guacamole at their table. It was some of the best guacamole I have ever had, and as a bonus, they served a hefty portion. Normally, I think Mexican restaurants skimp on the guac, but not Adobo Grill. It was incredible. For my entrée, I had ceviche, while Alex had a chicken cazuela (similar to a casserole). I had the citrus marinated mahi mahi with watermelon, mango, red onions, avocado, habanero. Again, it was the most delicious ceviche I have ever had AND it was served in a hefty portion. Adobo may have been my favorite restaurant of the weekend, so it is definitely a MUST!

What is Chicago without deep dish pizza? If you haven’t tried it, your trip is not complete. There are several area favorites like Lou Malnati’s and Giordano’s, but we chose to go to Gino’s East. Chicago deep dish pizza is something else and like no other pizza in the world. We got the garlic bread sticks along with the pizza we shared, but the bread sticks were unnecessary. Chicago pizza is very filling, so I’d recommend just ordering that. I’ve been to both Giordano’s and Lou Malnati’s and although I would be hard-pressed to pick a favorite, I really enjoy Gino’s because of the fun atmosphere and history. They are known for having people sign their names on the walls and something about that just feels very old world big city to me. I love it! In any case, wherever you go, eating some Chicago pizza is a must!

NIGHTLIFE:

After going to an afternoon Cubs game, we met with some of Emily’s friends for a drink at Vines on Clark. We sat in the patio because the weather was perfect! After a drink there, we headed to Sluggers, which has got to be one of my favorite fun bars! It is filled with skee ball, batting cages, and other arcade games. Although a lot of the machines did not work, we had a blast playing the games. Sluggers also has a dueling piano bar and a dance floor downstairs, so there is something for everyone!

One of my favorite bars was the Old Town Pour House, where we watched the Chicago Blackhawks play in one of their playoff games. Old Town Pour House is a huge space with one of Chicago’s largest draft beer selections. They have several huge TVs playing sports and a great atmosphere. Chicagoans are very into their sports and we had a blast cheering on the Chicago Blackhawks and were lucky enough to watch them beat the LA Kings in a double overtime.

Sunday night we met with some of my college friends at the J. Parker rooftop for drinks. This was without a doubt my favorite bar. It was a perfect evening to sit on the rooftop and enjoy drinks while catching up with friends. There was quite a nice selection of craft beers. My favorite part was the amazing views of Lake Michigan. This is definitely a great place to go on a date or with friends. If I lived in Chicago, I think I would be at the J. Parker every day for drinks.

Monday night, we had bought tickets for Second City: Best of Second City. I had been to Second City once before as part of a bachelorette party weekend and I had a blast laughing my butt off. This time was no different. In fact, they even performed one of the skits I had seen during my previous experience (without giving anything away, it involved a Chipotle burrito: amazing). Alex really enjoyed it as well. The members of Second City are very talented improv and sketch comedy actors and I was very impressed with some of the crazy things they came up with. Many famous comedians are alumni of Second City, including Tina Fey, Bill Murray, Chris Farley, Mike Myers, Dan Aykroyd, and Steve Carrell. I would definitely make a trip to one of the performances. I think any of them would be great!

DAYTIME ACTIVITIES:

Almost as soon as Emily picked Alex and I up from O’Hare, we quickly changed and grabbed a cab to head to Wrigley Field for a Cubs game. My family is big White Sox fans, so although I’ve seen the Sox, I have never had the experience of going to a Cubs game. We sat in the bleachers and had the best time. For $40, you cannot beat the bleacher seats. This is perfect if you aren’t a huge baseball buff like me. You are more in the party zone, while still being close to the action (you can even catch a few balls if you are lucky!). We got beers and Chicago hot dogs and settled into the sunshine to watch the game. It was a perfect afternoon! If you don’t want to go to the game, another option is to buy tickets to some of the bars across the street where you can watch the game from the rooftop while taking advantage of unlimited food and drink. Apparently the proposed renovations of Wrigley Field may interfere with this, so go there soon if you can!

Saturday morning, we went to the Green City Market Farmers Market in Lincoln Park for breakfast. We tried bacon cookies (they really tasted like bacon!), but the smoothies were the real winner. After leaving Green City Market, we briefly walked through the free Lincoln Park Zoo before walking along Lake Michigan to the Bean. The Lincoln Park Zoo was great and seemed like a popular destination. The “beach” at the Lake was filled with people running and exercising as well as a large group involved in a volleyball tournament. We even saw Giuliana and Bill Rancic and their baby running!

Of course we had to go to the Bean (officially titled Cloud Gate) and take touristy pictures. I would say it is the most touristy place in Chicago, but it is a fun and interesting piece of art and there are plenty of photo opportunities.

If you go to Chicago in the summer, you have to go to one of the many festivals. Fortunately, there was an art festival right in Emily’s neighborhood, the Wells Street Art Festival, so it was very convenient for us. Emily had several of her friends from grad school come over and we had drinks before heading out to the festival. There were live bands, drinks, food, and art and the weather was perfect! We walked around and explored before settling in by one of the bands. We spent most of the afternoon/evening there before heading to watch a Blackhawks playoff game.

Sunday morning, Alex and I decided to take a walk down State Street to look for the Playboy Mansion. Although it is closed to the public, it was fun to see. The homes on State Street are incredibly beautiful and I had fun playing with my Zillow app to see photos of the inside and take bets on the value of the exquisite homes. If you walk far enough down State Street, you will eventually get to many shops, such as Madewell, LuluLemon, Sephora, and more. We browsed a little before walking on to Washington Square Park. We sat in the park near McCormick Fountain and people watched while talking about how great our trip had been. It was a quiet and peaceful spot in the middle of the bustling city. I think it would be a perfect place if you had time for a little picnic. There was also an absolutely beautiful library there, the Newberry Library, but unfortunately it was closed.It looks beautiful, so if you are in the area, I would definitely stop by for a visit.

Monday, we met with my aunt and cousins at Navy Pier. We walked around and had lunch and drinks at Haray Caray’s Tavern. We had planned to do a boat tour together, but unfortunately, the weather did not cooperate. Instead, we all purchased the Chicago-famous Garrett popcorn (I recommend the caramel or the Chicago mix of caramel and cheese) and rode the Ferris Wheel. Since we couldn’t do a boat tour, my cousin’s husband was able to get us a brewery tour at Revolution Brewery. As I have mentioned in previous posts, one of my favorite things to do on a trip is visit a local craft brewery. Revolution has a really cool space, which they were remodeling into a larger tasting room, so I would love to see what it looks like when they finish the work. We had drank Revolution beers at J. Parker so it was especially fun to see where they are made, learn about how they are brewed, and taste other beers.

On our last morning in Chicago, we went on an architectural boat tour with Wendella Boats Lake and River Tour. It was fantastic and I was so glad we waited for clear weather! The tour started with an architectural tour of the river. Our guide was knowledgeable and funny and I enjoyed hearing about the different inspirations for many of the downtown buildings. My favorite was the Carbide & Carbon Building, which was built in the 20s and made to look like a champagne bottle.

Via ChiBoys Blog

Then the tour went through the Chicago Harbor Lock before going out to the Lake to see the best views I have ever seen of the Chicago skyline. The Wendella combo lake and river tour was 90 minutes and was more than worth the $28 fee. If you are really into architecture, you might want to consider the 75 minute river architecture tour, which spends the entire time on the river, but goes into much more detail. If you are just a tourist like us, I think the Wendella combo lake and river tour is the way to go!

I know there are about a thousand more things to do in Chicago, but we only had a few days, so these were my favorite activities from the trip! Please feel free to comment with your favorite Chicago memories!

I will leave you with one last photo from the trip. I saw this walking back to Emily’s one day: a girl painting a picture of the skyline. Look closely at her painting and you can see! I love this picture

RECAP: 

Eat:
Farmhouse Chicago: 228 W Chicago Ave, Chicago, IL 60654
Portillo’s: Locations across Chicago
Xoco: 449 North Clark Street (enter on Illinois St.), Chicago, IL 60654
Kanela: 1552 N. Wells, Chicago, IL 60610
Trattoria roma: 1535 N Wells St, Chicago, IL 60610
Garrett Popcorn: Locations across Chicago
Adobo Grill: 1610 N Wells St, Chicago, IL 60610
Gino’s East: 162 E Superior St (between Michigan Ave & St Clair St), Chicago, IL 60611

Drink:
Sluggers: 3540 N Clark St, Chicago, IL 60657
Vines on Clark: 3554 N Clark St, Chicago, IL 60657
Signature Lounge: 875 N Michigan Ave, 96th floor, Chicago, IL 60611
Old Town Pour House: 1419 N Wells Avenue, Chicago, IL 60610
J. Parker: 1816 N Clark St, 13th Floor, Chicago, IL 60614
Revolution Brewery: 2323 N Milwaukee Ave  Chicago, IL 60647

Visit:
Cubs game at Wrigley Field: 1060 W Addison St, Chicago, IL 60613
Green City Market: Wednesdays and Saturdays, 2732 N Clark St #302, Chicago, IL 60614
Lincoln Park Zoo: 2001 N Clark St, Chicago, IL 60614
The Bean/Cloud Gate: Millenium Park, 201 E Randolph, Chicago, IL 60602
Summer Festivals: City of Chicago Neighborhood Festivals
Washington Square Park/Newberry Library: 901 N Clark St, Chicago, IL 60610
Navy Pier: 600 E Grand Ave, Chicago, IL 60611
Second City: 1616 N Wells St, Chicago, IL 60614
Wendella Boat Tour: 400 N Michigan Ave, Chicago, IL 60611