Our first trip to Chicago certainly won't be our last.  Imagine a place that literally has everything you could possibly want from culture to food to entertainment, with people who treat you like they're from a small town in the South.  That's Chicago.

We took a train to Chicago which was awesome because we got to experience traveling on a train, which seemed a little weird and we saved money by not having to spend a crazy amount to park a car at our hotel over night.  We didn't waste anytime exploring after arriving to Union Station.

When it comes to amazing views from skyscrapers that touch the clouds, Chicago's got you covered. We recommend grabbing a drink at The Signature Room which sits atop the John Hancock building.

It's not the tallest building (that would be the Willis Tower), but it's free to go to the top unlike the Willis Tower.  However, you should be prepared to pay a lot more than you ever should for a drink.  Just savor it as well as the view.

When it comes to where to stay, check out the James Hotel right off magnificent mile.  It's a small boutique hotel with a lot to offer.

55 E Ontario Street
Chicago, IL 60611
(312) 337-1000

We found a great Taco restaurant in the Wicker Park area of the city.  This hipsteresque part of Chicago is loaded with restaurants and bars. We had lunch at Big Star.

We couldn't believe how reasonable the Tacos were with many under $4 a piece.  Order one of several different kinds to share.  It's the best way to try them.

Millennium Park is another must see destination in Chicago.
It houses the bean officially known as the Sky Cloud.

But this park has so much more to offer than just the bean.  


 It's loaded with incredible architecture.

When it came to finding the most authentic Chicago style slice of pizza, we did our research.  Pizza Due and Pizza Uno are the originals.  They actually serve the exact same menu, but Due was closer to our hotel.  Talk about authentic.  

When you walk into the restaurant, it's like walking back in time.  Be careful with the pizza, it's really hot.  Also, allow yourself plenty of time.  With deep dish pizza, it usually takes at least 30 minutes to cook once you place your order.  The servers there are great at reminding you of this.

619 N Wabash Ave
Chicago, IL 60611

Chicago is a food city, so we took full advantage of it.  RPM Italian made for a pricy but worth it dinner spot.  If you're looking to experience an old world Nona's kitchen, this isn't the place for you. RPM is very sleek in both decor and dish.

Go with the carbonra and the black squid ink pasta - you won't be disappointed.
52 West Illinois Street
Chicago, Illinois 60654
(312) 222-1888

We finished the night off with a trip to the Second City.  This comedy club is where many Saturday Night Live comedians got their start.  It's adult entertainment, leave the littles at home.

Fantastic photo bomb by the random dude behind us...

The Second City 
1616 N Wells Street
Chicago, IL 60614
(312) 337-3992

The next day we let our inner carnivore come out enjoying great steaks from a legendary steakhouse, Gibsons.  You could immediately tell the restaurant was a locals favorite.

Gibsons Steakhouse
1028 North Rush Street 
(312) 266-8999

Of course we had to check out Wrigleyville which is under a lot of construction right now.  Even though we are not big Cubs fans, Dave loves the Cards, Jess the Reds, we wanted to experience Wrigley Field first hand.  And of course the year we go, the Cubs win the World Series for the first time since Dinosaurs roamed the Earth.

This is a must do when in Chicago if you're a baseball fan.  The actual stadium doesn't have a lot to offer as it's really old.  But, you just have to respect the history.

While we were checking out Wrigleyville,  we had to stop at Al's Italian Beef, home of the great Chicago sandwich.  This was another food stop that Dave "had" to check off the list.

Chicago is full of unique food opportunities, Cupcake ATM included.  Stop by Sprinkles Cupcakes for a fun experience (kids would love this)!  You don't even have to go inside, just scroll through all of the delicious options, pop in your credit card and "ta-da"- your yummy cupcake appears!

Sprinkles Cupcakes
50 E Walton Street
Chicago, IL 60611
(312) 573-1600
(Between Michigan & Rush)

In addition to food, Chicago is a premiere shopping city.  If you find that you've walked and walked the Magnificent Mile and need a little boot of chocolate, check out Ghirardelli.  Order a Sunday of your choice, drop your shopping bags, sit at a window seat and enjoy the escape from the hustle and bustle while filling up on chocolate.

Ghirardelli Chocolate 
830 N Michigan Avenue
Chicago, IL 60611
(312) 337-9330

You can't go to Chicago without doing a little bit of shopping.  And if your dog is as lucky as ours, (you're welcome, Hopsen) you'll even bring back something for them!  Chicago is very dog friendly, which we loved and is home to cute boutiques for you guessed it, dogs.

Hopsen scored a pair of pajamas (seriously) and specialty pizza treats... we were in Chicago after all.
Although overpriced, it's worth the visit and Hopsen appreciated it.

Tails in the City
1 E Delaware Place 
Chicago, IL 60611
(312) 649-0347 

Chicago is an awesome city.  Since we visited in the summer, the weather was great and we were able to walk all over and check things out.  We had the best time just walking around the city.

If you have a chance to visit during the summer months, we suggest you go then. We are convinced that's when everyone visits who falls in love with the city and ends up moving there.

If you venture in the winter months, make sure to pack your warmest coat, a hat, gloves and warm shoes - you'll need them!

Fun little fact - Dave picked Chicago to spend a weekend with his guys for his Bachelor Party.  They went to a Cubs vs. Cardinals game, checked out Taste of Chicago and had the best time.  Chicago is a great city for celebrations and it is easily accessible for people regardless of where they live.
 Stay north of downtown.  DO NOT (we repeat, do not) go to the South Side.  It has one of the highest murder rates in the country.

Chicago has an incredible food festival in July.  If you're a foodie, we can't think of a better time to visit the city than when Taste of Chicago is happening.  Plus, you'll escape Chicago's frigid winter wind and temperatures if you go in the summer.

Try to avoid having a car in the city.  The cost of parking per night at hotels is quite a pretty penny.

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