Eating, Going, Planning

Chicago City Guide

If you have not already figured out, Kim and I love to travel. Because of this, it was only fitting that for my 25th birthday, one of the best gifts I could have gotten was a long weekend in the Windy City. For Memorial Day, I headed off on a late birthday trip to Chicago. Chicago had always been on my list of places to see eventually, but it was not at the top by any means. Now that I have been, I cannot wait to get back.  

Where to Stay: 

Thanks to some friends we know in Chicago, we stayed in the Gold Coast area. I cannot recommend this area enough. It was very safe, clean, had a lot of great food and drink options, and a close to just about anywhere. It was walking distance to Wells Street and Division Street, which was very convenient.  Our friends informed us that there are always great hotel deals going on in the area, so I would recommend keeping an eye out for those. Some hotels in the area that I would recommend:  

  • Hotel Indigo– This hotel has a really fun feel to it! In a great area, and consistently has wonderful reviews! Once you look at their rooms, you will fall in love with the colors and how original the hotel is! Certainly a fun hotel.  
  • Viceroy Hotel– The Viceroy is a brand new hotel right off of State Street. It is very closed to the Magnificent Mile, and right next door to what was our favorite pizza place! There is also a wonderful rooftop bar. I would highly recommend keeping an eye out for good deals on this hotel! It is a little pricey, but they apparently run great offers on their rooms.  
  • Claridge House– The Claridge House is a more affordable option in the Gold Coast. It is more on the “simple” side, but still beautiful with the great proximity to everything around!  
  • Thompson Chicago– The Thompson Chicago definitely fits the idea of luxury. There is a beautiful bar when you walk in, and a very upscale atmosphere. There is a great Italian restaurant inside the hotel as well. This hotel is close to the Magnificent Mile and a close Uber drive to almost anything around! 

Where to Eat: 

  • Lou Malnati’s– There is a lot of debate around Chicago’s best pizza, but there is no other place but Lou Malnati’s for me. Their pizza was incredible. I had to keep in mind it was deep dish, so after one and a half slices I was beyond stuffed. But hear me when I say the GARLIC BREAD was so incredible that we showed up every single day to enjoy it. Excessive? Yes. Worth it? Absolutely.  

Lou Malnati's Gold Coast

  • Stan’s Donuts– This was our very first food stop on our trip, and I can’t get over how cute it is! Their donuts are amazing, and they had good coffee, too. I do try to be gluten free as much as I can, so I was so happy to see they had my blueberry glazed donut  (along with many others) in a gluten free option. We even agreed that the gluten free tasted better than the blueberry old fashioned we also got!  Stan's Donuts Chicago
  • Portillo’s– While we had a hotdog at the ballpark, you can’t go to Chicago and not get a good Chicago dog! Portillo’s is famous for them! I definitely was not expecting it to be laid out the way it was. When you walk in, there are different counters for the hot dogs, sandwiches (the beef sandwich looked amazing), and their Italian station. It was busy, but there was plenty of seating and we got our food fast! I would definitely go back!  
  • Yolk– Yolk was a great little brunch place! They have locations all over and something for everybody on the menu. I’m a classic brunch girl with my eggs benedict. It was very good! Since it was 2 PM when we went, the other meal had was a buffalo chicken wrap, which was also very good! We also shared a Nutella crepe (because why not?), and it was great! 
  • Nutella Café – This little café was so fun! It is the only Nutella Café in the United States. They have all kinds of different Nutella themed pastries. Nutella is basically a food group in our family, so it was important to make the trek. They also have sandwiches and lunch-type items. This would be a great place to get some coffee and breakfast or lunch!  
  • Small Cheval– This was one of the greatest finds. After hours of looking for must eats in Chicago and every single one mentioning the famous Au Cheval burgers, I knew our itinerary wouldn’t allow for the wait that it is known to have (I do want to go back here sometime though). Only one site mentioned their daughter restaurant. When my friend also recommended it, I was excited to try to famous burgers at no wait. They were wonderful! I definitely want to try Au Cheval, but if you find yourself with limited time or on Wells Street, make sure to check this one out.  Small Cheval Chicago
  • Garrett Popcorn– Of course this isn’t a place to actually eat, but it is one worth stopping at! Our last few hours in Chicago, we made it a point to stop at one. My mom’s loves popcorn, so I made sure to get her some caramel corn before I left. She absolutely loved it! She said it was one of the best she has had. It is worth going for a souvenir or snack for your room! 
  • Harry Caray’s Tavern– We ate lunch here on the Navy Pier. It was really good. They are known for their BBQ. I got a pulled pork sandwich on a gluten free bun. It was probably the best gluten free bun I have ever had, and the pulled pork was amazing. The ribs were also said to be wonderful, and are what they are known for. If you are on the Pier and need a place to eat, I would definitely recommend this! 

What to Do: 

  • River Architect Cruise– One of my coworkers recommended this to me as soon as I found out we were going to Chicago. I wasn’t sure how I would enjoy this, but this was one of the best decisions we made to do! We did the river option that left from the Navy Pier. It is a big boat with bench seating that took us down the Chicago River. It was really cool floating between the skyline and hearing some of the history of Chicago. I will warn you, if you do this on a sunny day and do not get one of the covered seats, bring a hat, sunglasses, and sunscreen because we did get a little burned. They have a bar with water, sodas, beer, and wine, but you can bring your own water, too.  
  • Navy Pier– The Pier was really awesome! We ate lunch at Harry Caray’s (see above). In our City Pass, we got 4 rides each. We did the Ferris wheel and the swing. It’s a little bit of a walk to the end, but the lighthouse is fun to go see at the end of the pier. Along the way there are some places you can sit and relax including the Billy Goat Tavern and  Tiny-Tavern. When you make it to the end, stop at the Miller Lite Beer Garden for a drink and to relax.  
  • Sky Deck– The Sky Deck at the Willis Tower is one of the most famous attractions in Chicago. This is the glass ledge that goes out over the edge of the Willis Tower at 103 stories up. It was a cool experience, but also terrifying. Was it worth the 4 hour wait? Probably not. But we also were there on a long weekend. I would 100% buy a fast pass ahead of time or go with the City Pass (see below for tips to save money and skip lines). That money in itself would have been worth it to not go through that waiting again. Also it was SO hot upstairs because of all the people. If you go on a week day, go at 10AM when it opens to beat all the field trip groups. If you have no interest on going out on the ledge, but want a great 360 view from 100 stories up, see my next attraction. Sky Deck Willis Tower Chicago
  • 360 Chicago– This might have been my favorite thing we did the whole trip. Honestly, I would have just done this had I known how awful the wait at the Willis Tower would be. This is located at the John Hancock building. This, like the Willis Tower, had the 360 degree view from 100 stories up. The location was amazing because you could see downtown, the Lake, and Navy Pier from up there. There was a full bar with soft drinks, snacks, and alcohol. It was not crowded at all, and we loved just getting a soda and enjoying the view. You also have the option to do the “Tilt”over the side of the building. We did it just to say we did. It was probably not worth the money, but I am glad to say we tried it.  360 Chicago John Hancock
  • Fireworks– One of the best things I found was that Memorial Day Weekend-end of August, the city of Chicago puts on a fireworks show every Saturday and Wednesday. That Saturday was the first night they had them for the summer. We actually took a boat ride out into the lake away from shore. It was a 60 minute trip, and worth every single penny. It was a beautiful night and because of the location on the water, the fireworks looked as if they were going off above the skyline. It was a 15 minute firework show, and so much fun! Fireworks Lake Michigan Chicago
  • Millennium Park– Everybody knows of the famous “Bean” sculpture in Chicago. You could honestly spend a few hours in Millennium Park looking at all of the different art and enjoying the weather. We didn’t spend too much time here, but we easily could have.  
  • Cubs Game- If you are anything like me a love watching baseball, then this is a must! Of course the White Sox play on the south side of Chicago, too, but I have been wanting to get to Wrigley for a while now. It was a really cool baseball stadium. I love how it is one of the original stadiums, and it was a beautiful night complete with a perfect sunset over the ball park.  Millennium Park Cloud Gate The Bean

Where to Drink: 

  • Emporium– This was one of our favorite bars that we went to! It was a really fun arcade bar. We went here while waiting for our table at The Drifter (speakeasy noted below) to be ready. It was $.25/ token, and the $5 worth of tokens lasted us about 2 hours and we even had some left over! The drinks were very reasonable priced, and it was a lot of fun.  
  • Pops– Pops is a super cute champagne bar located by the Navy Pier. This is a much quieter bar. Also look into the speakeasy that is located in this bar for a little twist to your night. This would definitely be a fun place to go to before or after dinner one night.  
  • Cindy’s– This is one place I am so sad we didn’t get to go to. It is located right across the street from Millennium Park. This is a very beautiful rooftop bar with amazing views of the city. They also offer brunch, and you can make reservations for that if you are interested! If not, this would be a fun place to go to after seeing the park for a drink or two to enjoy the views and sunset.  
  • Green Door Tavern/ The Drifter The Green Door Tavern is a little bar a bit off the beaten path. It isn’t a bar I would go to just for the bar itself, but the speakeasy inside of it, The Drifter, is one of the few original speakeasy bars from the prohibition era. To get there you will go downstairs in the back towards the bathrooms. As you get to the bottom of the stairs there is a bookshelf on your right hand side that you’d otherwise walk right past. This is actually a door. There’s normally someone on the other side that you talk to and be put on the list. The wait for us was two hours, and they take your name and phone number to text you. Some wait upstairs at Green Door and get food and or drinks. We went to Emporium. You only have 5 minutes to get back once they text you. We got back in 8, and they thankfully still seated us. We were surprised when a cabaret show began right in front of us, but it’s all part of the experience! Speakeasy bar in Chicago
  • Hopsmith- Hopsmith was located on Division Street, which is close to where we were staying. There were quite a few fun bars including Mother’s (venture into there a bit later into your night). Hopsmith was our favorite of all the bars on Division Street, though. There is an upstairs, too, that is a little smaller and has a tap at your actual table, so if you and your group are beer drinkers, this is really fun! 
  • Wells Street- Wells street is just a few blocks down from Division. As mentioned, Wells Street has a lot of good food options, but also a lot of fun bars! Some of these include Old Town Pour House and Benchmark 

How to Get Around:  

Uber- Uber is the main way we got around. Honestly, if you want you can walk quite a few places, but it was really hot the weekend we went and didn’t have the best shoes. It was only about a $5-$10 Uber ride places. We made sure to plan things in the same area each day so we minimized on Ubers, but we never had a problem getting one and getting places fast. 

Train/Bus- I wish we had done more research on public transportation. Chicago has a lot of it, and I think had I known that (Houston doesn’t have great public transportation so I always forget), I would have planned this better because you can get most places you need to for very cheap. We did take the train from the airport to as close as we could to the Gold Coast area then Ubered from there, which was a lot cheaper than the Uber the whole way. Honestly we just Ubered the way back to the airport, and it was a lot more convenient so it is up to you if you want to spend a little more, but the train worked out just fine.  

What to Pack:  

  • Sunscreen– This came in handy especially during the sunny days on the Navy Pier! The summer in Chicago can be very bright, so make sure to cover your arms, neck, and legs, too.  
  • B.B. Cream– This is my favorite B.B. Cream because it has great coverage, but doesn’t make me feel oily through the day! It also has great SPF and protection.  
  • Birkenstocks- You do a lot of walking in Chicago. Supportive shoes are needed, and I love traveling with my Birks. They are both supportive and cute.  
  • Side Purse– This was perfect to have next to me. It carried my Chapstick, sunglasses, wallet, and a few other things like sunscreen to have with me all day. It’s nice to have a crossbody while walking around a lot that doesn’t get too heavy and you can keep close to you.  
  • Portable Charger- We were gone all day and of course taking a lot of pictures. This was so nice to have on me to help reapply any makeup and also keep my phone charged for the day.  
  • Glam Glow– My skin definitely 
  •  got dry from traveling. This was as usual a life saver to help my skin feel and look refreshed the next day!  
  • Sunglasses– It was very sunny during our trip! A good pair of sunglasses was needed during the days. 

Other Information: 

Go Chicago Card– We purchased the 4 pack Go Chicago Card tickets. This was really convenient because there is an app and they can just scan it at the locations you go to. There is a list of all the places you can use it at on the website. It allowed us rides on the Navy Pier, the Sky Deck, the 360 Viewing Deck, and the Architecture cruise. This would be a great one to do on a week day or not busy weekend because it is the cheapest, but no fast passes included. 

Chicago CityPASS– This is the one I wish I had gone with. It is a little more than the Go Chicago Card, but it allows you fast passes. We waited 4 hours for the Sky Deck. With the CityPass, you can skip many lines at the Sky Deck and the 360 Viewing Deck. Going on a busy weekend like Memorial Day, I wish we had paid a little bit more for these passes. It would have saved us a lot of time and allowed us to do a few more things on the list! 

Have you been to Chicago? What are some of your favorites? 



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