I visited the windy city 3 years ago with a gaggle of old college friends. It was early October, aka perfect weather everywhere, and we were all fresh to the city and reuniting after missing each other several months, so needless to say it was a pretty awesome trip.
We went out in every neighborhood, ate deep dish pizza (twice!), met nice Midwest boys and took copious amounts of selfies at the Bean. I fell head over heels in love with Chicago.
Then, like any smitten school girl, I ruined it all a couple months later with a mid-January follow-up trip. (I blame you, cheap Southwest flights!) I froze my lil toosh off for 4 days and then kept my jetsetting bicoastal.
I went back last week with Ev and friends to attend a wedding and it was such a splendid short trip. From waking up to a view of the river & the smell of fresh chocolate (seriously… who is lucky enough to live down the street from a Chocolate Factory??!), to fireworks in the rain over Navy Pier, to private rooftop pools, it was a pretty perfect weekend. This was my first time in Chicago over the summer, and boy do they do a good job keeping that city pretty! Even the busiest streets downtown are kept pristine, so you never have the trash/urine-infused NYC
eau de city stank. As for the weather, it sure wasn’t perfect – thunderstorms and 90% humidity and rain …but maybe 5 years in New York has finally started to weather my soft California tolerance.
Below list is an aggregate of my 3 rendezvous there, and is by no means comprehensive. Chicago, I’ll be back to explore more!
Sights: Any guidebook or internet search will tell you these, but you’ve got to see them anyways!
- The beautiful Cloud Gate & surrounding Millennium Park (it becomes an ice skating rink in the wintertime). It’s nicknamed “the Bean” and gorgeously reflects the city’s skylight & clouds above.
- John Hancock building & the Sears (Willis) Tower
- Check out where they filmed the long truck/car chase scene from the Dark Knight – it’s in the underground “freeway”/shortcut called Lower Wacker. This is a pretty good recap of all the top spots if you’re big into Batman.
- The famous Wrigley Field in Lincoln Park
- Navy Pier: stroll by the water, see the touristy ferris wheels, and enjoy markets & live music in the summer
- The Shedd Aquarium: amazing and pretty comprehensive though it’s no Atlanta Aquarium
Food (!!!) & Nightlife:
- The deep dish pizza debate: Giordano’s or Lou Malnati’s. I personally love love Lou Malnati’s – their pizza is more tomato based. Giordano’s is too cheese-heavy (and I LOVE cheese… this pizza is just a little too… stringy & tough)
- Portillo’s, Hot Doug’s, Potbelly and any other Midwest chain that dumps sweet peppers over everything = A+ in my book
- Meat meat & more meat (I was basically at a college football reunion with these guys…): Hefty burgers at Porkchop on the West Loop & Bacon wrapped sausages at Kaiser Tiger, oops there go my arteries!
- Old fashioned doughnuts in a little nook called Doughnut Vault near River North.
- If you’re up in the North River, stop by Yolk for some amazing, classic American brunch
- Make a pitstop to Weiner Circle at the end of your night, order a “black milkshake” and make sure you have some cash on you
- Greek Islands in Greektown: Some of the BEST Mediterranean food I’ve ever had: Tender Octopus, Saganaki (flaming cheese) & trying Taramosalata (candy pink Greek caviar) for the first time
- Rooftop on the Wit Hotel, The Aviary, The Violet Hour = fancy shmancy cocktail magic
- Jazz & 4am nights at Green Mill uptown. (Most bars close at 2am in Chicago)
- Bar hop around Wicker Park, Lakeview, Lincoln Park, Edgewater & many more amazing pockets of Chicago I’m sure I’m missing!