Chicago - Weekend Getaway

Chicago Weekend Getaway - only have a few days in Chicago? Here is a list of things you MUST see and EAT! Plus a rooftop bar with the BESt view of Chicago! Add these places to your list!

Chicago Weekend Getaway - only have a few days in Chicago? Here is a list of things you MUST see and EAT! Plus a rooftop bar with the BESt view of Chicago! Add these places to your list!

At the end of June, we took a quick trip to Chicago. We haven't been to Chicago in about 7 years! I can't figure out why we stayed away so long? We had THE BEST time!  I am already planning on going back next year.

The main purpose for our trip was to see Hamilton. Have you seen it? O-M-G! AMAZING! We both absolutely LOVED it. I highly recommend trying to snag a ticket when it goes on tour. I'm dying to see it again. It was 1000% worth the trip to Chicago.

We did a little sight seeing and a lot of eating. We found a rooftop bar with THE BEST views of Chicago and ate at one of the best restaurants EVER! I am really anxious to get back to The Windy City!


Uno Pizzeria
Cheese Sticks at Uno Pizzeria in Chicago
We dropped off our bags at the hotel and headed straight out in search of pizza.
There were three "famous" deep dish places within walking distance of our hotel.
I let Chicken Legs pick and he chose Uno. 

We started with some cheese sticks.

Cheese Sticks at Uno Pizzeria in Chicago
I could eat my weight in these cheese sticks! SO good!!

Numero Uno Pizza at Uno Pizzeria in Chicago
We both got individual pizzas.
Chicken Legs got the Numero Uno

Numero Uno Pizza at Uno Pizzeria in Chicago
It was loaded with Sausage, Pepperoni, Onions, Peppers, Mushrooms, Chunky Tomato Sauce, Mozzarella And Romano.

Prima Pepperoni Pizza at Uno Pizzeria in Chicago
I got the Prima Pepperoni and added sausage.

Prima Pepperoni Pizza at Uno Pizzeria in Chicago
LOVE!!!

Uno Pizzeria
29 E Ohio St, Chicago, IL 60611
Phone: (312) 321-1000

Chicago Weekend Getaway - only have a few days in Chicago? Here is a list of things you MUST see and EAT! Plus a rooftop bar with the BESt view of Chicago! Add these places to your list!
After lunch we waddled down Michigan Avenue.

Chicago Weekend Getaway - only have a few days in Chicago? Here is a list of things you MUST see and EAT! Plus a rooftop bar with the BESt view of Chicago! Add these places to your list!

The Bean at Millennium Park in Chicago
We stopped by The Bean.

The Bean at Millennium Park in Chicago

Mandatory selfie!

The Bean at Millennium Park in Chicago

The Bean at Millennium Park in Chicago

Millenium Park
201 E Randolph St, Chicago, IL 60602
Phone: (312) 742-1168

Abraham Lincoln statue on Michigan Ave in Chicago
We passed this statue of Abraham Lincoln talking to Nick Saban about his play calling.
Just kidding! We really don't know who the man with Lincoln is. 
We asked some locals, and they didn't know either.
We went with Saban, because it totally looks like him! LOL!

Ditka's
Pot Roast Nachos at Ditka's Restaurant in Chicago
We had dinner reservations at a different restaurant in Chicago. After looking over all the reviews, we decided to ditch our original choice and go with tried-and-true Ditkas.
Our hotel was close enough that we could walk to dinner.

We started with the famous Pot Roast Nachos.

Pot Roast Nachos at Ditka's Restaurant in Chicago
We got the small order. We could not stop eating these nachos!
SOOOOO good!!!

Steak at Ditka's Restaurant in Chicago
Chicken Legs got a big fat steak for dinner.

Filet Sliders at Ditka's Restaurant in Chicago
I went with the Filet Sliders.

Chocolate Layer Cake at Ditka's Restaurant in Chicago
We shared the Chocolate Layer Cake for dessert.
Massive!!!!

Ditka's Restaurant
00 E Chestnut St, Chicago, IL 60611
Phone: (312) 587-8989


John Hancock Building in Chicago
Our hotel was literally next door to the Hancock Building.
We didn't go up to the top on this trip. 
We've been before, but will definitely add it our next itinerary.

John Hancock Building in Chicago

 Eataly
Prosciutto and Fresh Mozzarella at Eataly Chicago
I was SUPER excited to get to try Eataly on our trip.
Eataly is Mario Batali's Italian market. 
There are several restaurants and TONS of amazing Italian foods to purchase.

We ate the best Italian food of our lives here.
It was so good, that we ate here twice on our short trip!

Our first trip we ate at La Pizza & La Pasta.

We started with the Prosciutto and Fresh Mozzarella.
I'm still dreaming of this goodness!

Cacio e Pepe (Pasta with Cheese and Pepper) at Eataly Chicago
The Cacio e Pepe (pasta with cheese and pepper) was to-die-for!

Rustica pizza at Eataly Chicago
Finally we had some pizza. We built our own.
Rustica dough, San Marzano tomato sauce, Mozzarella di Bufala, Salame and Mushrooms.
It was crazy good! Wishing I had the leftovers right now!

Ragu Arancini (fried risotto) at Eataly Chicago
On our second visit, we ate at La Piazza.

We started with an Arancini (fried risotto).
It came out looking like a pear. I've only had round arancini, so this was different.

Ragu Arancini (fried risotto) at Eataly Chicago
This is the Ragu Arancini - Saffron risotto, bolognese, green peas, cacio di roma.

Amatriciana Roman Style Pizza at Eataly Chicago
We shared a Roman-style pizza.
I wanted to see how it differed from the pizza the previous day.

Amatriciana Roman Style Pizza at Eataly Chicago
We got the Amatriciana
Tomato sauce, crispy salumi, red onion, cacio di Roma cheese, chili flake


Amatriciana Roman Style Pizza at Eataly Chicago
Delicious with a little kick.
I want to come back to eat dinner at some of the other restaurants in Eataly.
It was SO MUCH FUN! 

Tiramisu Cannoli at Eataly Chicago
We couldn't pass up the Cannoli Bar. 
This is the tiramisu cannoli. YUM!

Fresh Nutella and Strawberry Crepe at Eataly Chicago
We also got a fresh made crepe with Nutella and strawberries.
Basically, Eataly is my heaven on earth.

Eataly Chicago
43 E Ohio St, Chicago, IL 60611
Phone: (312) 521-8700

Architecture River Tour
Architecture River Tour in Chicago
One of the architecture tours is a MUST when you are in Chicago.
There are several companies that offer tours, and I think they are pretty much the same.
This trip we toured with Shoreline Sightseeing at Navy Pier.
The boat was nice and the guide was great.

Architecture River Tour in Chicago

Architecture River Tour in Chicago
These honeycomb buildings are so fun!

Architecture River Tour in Chicago

Architecture River Tour in Chicago

Architecture River Tour in Chicago

Architecture River Tour in Chicago
LOVE the reflection!

Architecture River Tour in Chicago

Architecture River Tour in Chicago

Architecture River Tour in Chicago
LOVE this photo! I absolutely love all the reflections in the buildings.

Architecture River Tour in Chicago

Architecture River Tour in Chicago
This building has a map of Chicago on it.
The red dot is the location of this building.

Architecture River Tour in Chicago
You get great views of the Sears Tower/Willis Tower.

Architecture River Tour in Chicago
We didn't make it over here to go to the observatory.
Next time.

Architecture River Tour in Chicago

Architecture River Tour in Chicago
Chicago, you are SO colorful!

Shoreline Sightseeing
600 E Grand Ave, Chicago, IL 60611
Phone: (312) 222-9328

Gibson's Steakhouse
Carpaccio at Gibson's Steakhouse in Chicago
Gibson's is our favorite steakhouse in Chicago. 
This was the first dinner reservation we made after we booked out trip.

We started with the Carpaccio.
Divine.

Gibson's Steakhouse in Chicago
Chicken Legs got a gigantic steak!

Brussels Sprouts and Bacon at Gibson's Steakhouse in Chicago
He also got some Brussels Sprouts with bacon.

Gibson's Steakhouse in Chicago
I opted for the filet.

Gibson's Steakhouse in Chicago
It was cooked to perfection.

Twice Baked Potato at Gibson's Steakhouse in Chicago
We also shared the Twice Baked Potato. SO good!



Macadamia Turtle Ice Cream Pie at Gibson's Steakhouse in Chicago
We couldn't pass up one of their crazy big desserts.

Macadamia Turtle Ice Cream Pie at Gibson's Steakhouse in Chicago
Behold the Macadamia Turtle Pie - that is ice cream covered in macadamia nuts in a cookie crust smothered in chocolate.
Hold me!

Gibson's Bar & Steakhouse
1028 N Rush St, Chicago, IL 60611
Phone: (312) 266-8999


 Hamilton
Hamilton in Chicago
The reason we came to Chicago.
It was fabulous. I highly recommend it!
The tickets were crazy expensive and worth every single penny.

 Cindy's Rooftop Bar
View from Cindy's Rooftop Bar in Chicago
After the show, we walked straight to Cindy's Rooftop Bar.
The bartender at the hotel recommended it to us and the recommendation was spot on.

View from Cindy's Rooftop Bar in Chicago
How amazing are these views of Chicago?!?!

View from Cindy's Rooftop Bar in Chicago

View from Cindy's Rooftop Bar in Chicago

View from Cindy's Rooftop Bar in Chicago

View from Cindy's Rooftop Bar in Chicago
Since we were there, we enjoyed a cocktail with a view.
GO TO CINDY'S!!!

Cindy's Rooftop
12 Michigan Avenue, Chicago, IL 60603
Phone: (312) 792-3502

 Maple & Ash
House Smoked Maple Glazed Bacon at Maple & Ash in Chicago
This is another recommendation from the bartender at our hotel.
It was THE PLACE to be! The restaurant was hopping!
There is a bar downstairs and the restaurant is upstairs.

We started with the House Smoked Maple Glazed Bacon because - bacon!
It is on the menu as a side dish, but we just dove right in!


Caesar Salad at Maple & Ash in Chicago
Chicken Legs got a Caesar Salad - wood-fired romaine, pecorino, soft cooked egg & savory sprinkles
He said it was THE BEST caesar salad he's ever eaten.
He's eaten a lot of caesar salad in his time, so that says a lot.

Australian Lamb Chops at Maple & Ash in Chicago
For his entree, Chicken Legs got the Australian Rack of Lamb.

Australian Lamb Chops at Maple & Ash in Chicago
He loved it!

Au Gratin Potatoes at Maple & Ash in Chicago
We had to get the Au Gratin potatoes because I NEVER pass up au gratin potatoes.


Prime Beef Meatballs with cheese curds and garlic bread at Maple & Ash in Chicago
For my entree, I went with the Prime Beef Meatballs.

Prime Beef Meatballs with cheese curds and garlic bread at Maple & Ash in Chicago
They were served in caramelized tomato sauce with cheese curds & garlic bread.
It is an appetizer, but I definitely made a meal of it.
It was INSANELY delicious!
I want to fly to Chicago just to eat this again.
I'm not even joking.

Chocolate Banana Bulleit Bombe at Maple & Ash in Chicago
Since we didn't have much to eat already, we got dessert. LOL!
This is the Chocolate Banana Bulleit Bombe.
They pour warm Bulleit Bourbon Caramel on top of the chocolate domed dessert right at the table.
It was heavenly!

Maple & Ash is a new favorite. It is a MUST on your trip!

Maple & Ash
8 W Maple St, Chicago, IL 60610
Phone: (312) 944-8888

Ritz Carlton - Chicago
 Ritz Carlton Chicago Room
We stayed at the Ritz Carlton on Michigan Avenue.
It is in the Watermark Place and next door to the Hancock building.
When we checked in, they upgraded us to a corner suite!!!!

Ritz Carlton Chicago Room

Ritz Carlton Chicago Room

Ritz Carlton Chicago Room
I LOVE the Asprey products at The Ritz Carlton.
I *might* steal them all to use at home.
We had two bathrooms in our room, so I stocked up!!!!

View from Ritz Carlton Chicago Room
We had a great view from our room.

View from Ritz Carlton Chicago Room

View from Ritz Carlton Chicago Room

View from Ritz Carlton Chicago Room
They were redoing the restaurant and rooftop bar while we were there.
We made the best of it. 
The bartender, Mel, was great. 
He is the one that told us about Cindy's and Maple & Ash. 

I drank lots of prosecco. 
Chicken Legs likes to tell people that prosecco is my middle name. He thinks it's funny.
I think some of them believe him. LOL!

Grilled Chicken Club from Ritz Carlton Chicago
We ate lunch in the restaurant before we headed to the airport.
The Chicken Club was great!

I can not wait to go back and see the newly renovated bar and restaurant.
It opened the week after our trip. Boo!!!
I guess that is our reason to go back to Chicago!

What are your favorite places to eat in Chicago?
Anything we MUST do on our next trip?
Leave me some suggestions!!!





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7 comments

  1. We have so many favorites in Chicago. We always to go the Purple Pig. And we love Twin Anchors Ribs. Last trip we went out to Wicker Park and tried Big Star Tacos. It's a Paul Kahan restaurant. The food is great, and the atmosphere is so fun. Across the street is a hidden bar, The Violet Hour. The front of the building is covered in graffiti, and there is just a single door with a doorman that stands outside to let you in. Y'all should check it out!

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  2. Stephanie-- great-sounding trip. Your "stuff" doesn't scroll down well for me. Is it my computer?

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    1. I would say that it is your computer- it scrolls fine on mine and no one else has had any issues.

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  3. We have been contemplating Chicago. We've never been. This post is definitely tempting us more! Do you have a hotel reccomendation?

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  4. I spent 24 hours in Chicago last year and wish I could have fit in the boat architecture tour! All of this food looks amazing! I wish I had an Eatlay closer, I loved everything about it. Sounds like an amazing getaway!

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  5. I live close to Chicago and usually take weekend trips at least once a month. You mentioned so many of our favorites. Chicago really is a beautiful city!

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  6. Lowry's...you HAVE to go. Expensive, but seriously the best prime rib ever!! They roll it to your table in a big cart and carve it for you. The chocolate paper bag dessert was awesome. That same weekend, we ate at Billy Goat Tavern (think Saturday Night Live---cheeburger, no coke--pepsi). And we also had brunch at Signature Room at the 95th--Hancock Bldg. Sooooo good!!

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