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Chicago

We spent one day exploring Chicago before we embarked on our Route 66 trip. Of course we couldn’t do everything, but we were happy with what we fit into the tight schedule. Here’s my city guide:Chicago Route 66

STAY: Because we had a car, we stayed in an Airbnb apartment in order to save money on the SKY HIGH parking fees that hotels charge in Chicago. Our apartment rental was in a great location! We had a wonderful view of the city skyline, Willis Tower, and the lake. It was a long walk to Millennium Park and the Art Institute of Chicago, but the view made up for that.

Chicago Route 66Chicago Route 66

EAT: When you’re in Chicago, you have to try some Chicago foods, including deep dish pizza. We stopped into Lou Malnati’s Pizzeria for deep dish pizza. The mister liked it. It was good, but I think that was my first and last deep dish pizza.Chicago Route 66Chicago Route 66 Lou Malnati's

SEE: We walked to Millennium Park and checked out Cloud Gate, aka The Bean. It was fun watching everyone taking photos of themselves. Chicago Route 66 Cloud GateChicago Route 66 Cloud GateChicago Route 66 Cloud Gate

After doing some selfies in the Bean, we did a quick tour of the Chicago Art Institute. We saw American Gothic, Seurot’s A Sunday on the Grande Jatte, several Van Gogh’s including his painting, The Bedroom. But the piece I would have taken home is John D. Graham’s Cave Canem. I love the pink color, the greenish little Chihuahua and her pose.Chicago Route 66 Art Institute of ChicagoChicago Route 66 Art Institute of ChicagoChicago Route 66 Art Institute of ChicagoChicago Route 66 Art Institute of ChicagoChicago Route 66 Art Institute of ChicagoChicago Route 66 Art Institute of Chicago

We then walked around and explored more of Chicago.

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MORE EAT: For dinner, we had to eat some more typical Chicago food and the mister wanted a Chicago-style hot dog. So we drove out to Gene and Jude’s. The place is a sausage-fest. Literally. There were like 20 guys working behind the counter. And the Mister was happy because all of them had Chicago accents. (Everyone else we encountered must have been a transplant.) He liked the hot dog, but I didn’t think it was that special. The french fries were fresh and tasty!

Chicago Route 66 Gene and Jude'sChicago Route 66 Gene and Jude's

The best thing about Gene and Jude’s was that it was located right next to a Tiki Bar! What are the coincidences? We enjoyed a couple of drinks at the Hala Kahiki Lounge with the pufferfish lamps to celebrate the start of our Route 66 trip.Chicago Route 66 Hala Kahiki LoungeChicago Route 66 Hala Kahiki LoungeChicago Route 66 Hala Kahiki Lounge 

What we missed: Willis Tower, Billy Goat Tavern, Wrigley Field, Wicker Park, an architectural cruise, and the beach.

Have you entered my Route 66 Giveaway? Enter for a chance to win a canvas tote stocked with some of my favorite Road Trip essentials including a travel journal, iTune’s gift card, sunglasses, and more! Click here to enter.

Route 66 Road Trip Essentials Giveaway

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