Pick Me Up isn't my favorite of Chicago's cafe's, but it's late hours definitely makes it an ideal spot for a late night meal or date location. Their pies are awesome, and the vibe is much chiller and laid back than most other places in Wrigleyville.
Awesome food, and awesomely cheap. If you're looking for something quick and filling, check out Papa Hassan's and grab yourself the chicken shwarma.
The Jay is a total dive, but it's an Omaha landmark. My mom used to regale me with stories of her time at the Jay in college, and not much seems to have changed since, including their prices.
Way off the beaten path, the Little Wild Horse Canyon is great for a day hike if you've already seen Goblin Valley State Park next door. Bring lots of water, and be prepared to do some tricky navigation on your own, since there aren't many sign posts along the way.
One of those classic things that you pretty much HAVE to see if you have any time at all while traveling along i-90. It's a hilarious photo op, and how many other green giants can you say you've been to?
The. Greatest. Hike. Ever. The views are jaw-dropping, the hike is exhausting, and the prospect of making your way to the top along support chains anchored into the rock is terrifying, but if you're up for it you absolutely have to do Angel's Landing.
Elkmont is a totally cool area to explore. It's got a whole street of abandoned houses that are still surprisingly intact, and some really beautiful hiking trails as well.
The coolest office space in a former brewery you've ever seen. Not only does Roadtrippers have a freaking awesome ArtWorks mural on the southern wall of the building, but the two floors of underground tunnels are hands down the most awesome place to explore in the entire city.
Very basic but quite cozy cabins just outside of Bryce Canyon National Park. I'd highly recommend staying here and driving into the park if you're considering an extended stay in the area.
I'm not sure what was cooler, the drive up to Pikes Peak, or the views when you finally got there. It's a breathtaking drive with a ton of switchbacks, and when you get to the summit you feel like you're on top of the whole world (you can also ride the cog train up, which I hear is pretty rad too). Be sure and try the amazing donuts they make at the summit!
Two things to watch out for before you drive up: First, have a half tank of gas in your car--they ask you about this when you pay the entry fee, but there isn't a gas station in the area so make sure you're well-stocked in Colorado Springs before starting the drive. Second, they aren't kidding around when they tell you to put your car in low gear. I forgot to on my way down and was riding my brakes all the way until the mandatory brake check, at which point they told me that my brakes were riding dangerously hot and made me wait for about 20 minutes or so until they had cooled down.