Yes, I travel in heels 💁🏼 It is only a 48 minute flight (54 according to my friend 😜) and we hit the ground running once we arrive! Haha plus I am usually wearing heels. Our trip is from a Thursday to Sunday and I think that is the perfect amount of time for anyone! If you plan on doing more sightseeing you may want to add an extra day!
Hotel:
We stay at The Thompson hotel. We love it for several reasons, but the location for us is #1. Right in the heart of the Viagra Triangle (yes it is an actual location choice on Instagram 😂). No we do not stay there for that reason, but there are so many good restaurants and most of the shopping is within a 4-5 block radius! The hotel itself is very cool yet sophisticated with a great bar and restaurant on site, Nico. The staff are accommodating and definitely remember us each time we come back, yet I haven't decided if that is a good thing or not. ☺️
Off season pricing for our trip in May where we traveled with our 4 year old daughter was around $160 a night, so very affordable. During high season, you can expect that price to double.
Dining:
Portillo's- famous hot dogs, because when in Chicago!
Maple & Ash- upscale dining, cool bar scene and great food. I would say kid friendly if they are over the age of 10. Otherwise it is a great date night!
Turquoise- It is a Turkish restaurant about a 15 minute Uber ride from The Thompson, but the food is worth it. Two of my friends that I travel with are Turkish.
Hugo's Frog Bar- My favorite Key Lime Pie in Chicago but please only get one dessert there for a table of 4 or more. It is way way too much! This is also the fist place I tried frog legs 😳 We took our 4 year old here and she was fine so I would say it is kid friendly for the most part. The noise level is pretty high at peak dining times.
LuxBar- Across the street from The Thomson. The avocado toast is amazing, the truffle fries are yummy and it's also a great place for a patio happy hour.
Fig and Olive- Upscale with a cool indoor bar. I have been here for brunch and lunch and to be honest, the brunch was my favorite! I would say not very kid friendly either.
Lou Malnati's Pizza- I have not had the "other" cometetiors pizza, Giordanos, but the crispy, buttery crush from Lou's definitely won me over! I asked a local what his favorite pizza was and he suggested Pequods, so we will try that next time!
Sprinkle's Cupcake Machine- I mean it's an ATM for cupcakes, definitely must try it!
Federales- Tacos and Tequila! Fun Mexican restaurant if you are craving it! Open roof and fun vibe weekend days!
RM Champagne Salon or Pops for Champagne- if you are looking for a fun place to sip some bubbly!
RL Restaurant- We grabbed lunch here this last visit and we were all concerned on what to wear but honesty it was preppy but not stuffy. It is a place to say that you have eaten at.
Spiaggia and Spiaggia Cafe- We had a cocktail at the Spiaggia bar waiting for our table in the cafe part. I loved the atmosphere and view much better than the cafe view. The food is very small portions, fancy, and I would say if you are a "foodie" you would love it. It is unique and the flavors are great.
Little Goat Diner, Duck Duck Goat & Girl and the Goat- These were also recommendations from a local and we will definitely be trying one of these on our next visit! All ran under same Executive chef who won Bravo's Top Chef title.
Gibson's Italia- Great rooftop bar for Summer, and the vibe and scene is hip and similar to Maple & Ash. This is different that the Gibson's across from the Thompson hotel.
Bellemore- A new Artistic American cuisine restaurant that my friend Jentry recommends in the West Loop. She said the food is amazing!
Monteverde- A great place for brunch or dinner! They hand roll the pasta right there in house and they have a great bar and rooftop patio open in Summer.
Tempo Cafe- We ate here for breakfast but a full menu is served all day long and you can bring your own booze until 10pm.
The Pancake House- This is our go-to breakfast the day we leave Chicago! It is directly across the street from The Thompson. The omelettes are huge so you can share one! Obviously the pancakes are delicious.
Nightlife-
Nightlife in the Summer is all about rooftops! Probably because just like here in Des Moines, the weather is finally nice and people want to get out and enjoy it as much as possible.
The Godfrey Hotel- A little older crowd with a nice rooftop bar.
Cyndie's Rooftop- Located at the Chicago Athletic Club on South Michigan, this bar hits the younger crowd.
Untitled- It is called a "supper club" because you can eat there too and you will think it is bizarre when you first walk in but later on it livens up! We just went there for dancing and a lot of it!
Underground- Exactly what it says. It is a nightclub that is underground. I remember it being fun but that is not saying much 😂
Chicago with a Toddler:
Shedd Aquarium- I think it is so much easier to get tickets online ahead of time! The line can get long. There is so much to see! If you want to do the shows, make sure to get tickets as well and plan your day round those times! Oh and parking was terrible because it was super busy the day we went but we found a parking garage not too far away.
American Girl Doll- it is an experience....an expensive one at that, but you must do it at least once if you have a doll loving child.
Lincoln Park Zoo- 35 acre zoo with FREE admission and open 365 days a year! It is actually one of America's oldest zoos too! Check out their website for other zoo events HERE. (If you have a Blank Park Zoo membership you will receive 10% off food and merchandise.)
LegoLand- This is indoors at a Mall in Schaumburg, but it includes lego themed rides and a softer play area for the littles. Booking your tickets ONLINE is actually cheaper!
Rainforest Cafe- I feel like if you have been to one you have seen them all, but if you haven't ever dined at one, you should go at least once.
Maggie Daley Park- This park is so fun! Also fun in the Winter with an ice skating ribbon around the park. It also features climbing walls, tennis courts, open picnic areas and a 3 acre children play garden. It's open from 6am-11pm and features 6 different play areas, including: The Wave Lawn, The Harbor, The Watering Hole, The Slide Crater, The Enchanted Forest, and The Sea.
Chicago Children's Museum- This is located at The Navy Pier! Be sure to check the dates and times for fun events and also a free family night.
The Field Museum of Natural History- (You can use your Des Moines Science Center membership here) It holds Dinosaur exhibits, Underground and Egypt adventures. I would say this is more appropriate for children over 5.
The Adler Planetarium- (Also included with your DSM Science Center membership) This is for those littles who are interested in all things Space!
If you are planning on seeing a few of these sites on 1 vacation, you may want to check out the Chicago GO PASS for discounts!
I hope this list of fun things to do gets you started on your Chicago vacation! If you have other must see things or restaurant recommendations please let me know because I will definitely be back! XO
