Chicago 48 Hrs
48 hrs is a 2-day itinerary designed to not only take you by the main attractions but also to conveniently locate the best food & drink options along the way. Cheers!
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Let’s get to it.
Chicago
Chicago is the city of broad shoulders. The Windy City. The home of deep dish pizza! And so much more. Dive in and welcome to Chicago!
Map
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Day 1
Day 1 starts off with the Art Institute of Chicago. With famous works such as George Seurat’s “A Sunday on La Grande Jatte,” Pablo Picasso’s “The Old Guitarist,” Edward Hopper’s “Nighthawks, and Grant Wood’s “American Gothic.” You’re not going to be disappointed with this collection. The museum also includes a newly revamped modern art wing, as well as African and Indian art, Ancient Byzantine, and textiles. The Art Institute has been known to hold music festivals and after dark parties, so keep your eye out for those dates.
Pop across the street to Cindy’s for a fresh tasting cocktail or a glass of wine and soak in the day with beautiful views overlooking Millennium Park and the city, out on the terrace.
Next, head north and be prepared for the slightly overwhelming Magnificent Mile. This might be the most congested part of the city, and absolutely magical during the Christmas season.
After shopping at Tiffany’s (I kid) I’m sure you’ve worked up an appetite. Cruise along Rush st and pop into Nico Osteria. There might not be a spot available in the restaurant, but they have a beautiful, airy salon bar that offers the same delicious food and wonderful cocktails. A great spot to catch your breath.
Next, head north a little ways and stop in at this Gold Coast location, La Colombe cafe. Philly based, these guys have entered Chicago and have left their mark. They feature world class coffee, with a nod to those that stop in for coffee and conversation. Everything is thought out here, as they prepare and hand off your espresso drink.
*If you wanted, take a quick peak over at Lake Michigan at Oak St beach. It would be a shame not to see the blue water of one of the largest fresh lakes in the world.
Next is Lincoln Park. It offers a vast array of paths and benches to sit along. Enjoy your coffee here or keep walking through. The zoo, which is located a little more north, is free and offers a look into a gorilla house and even a polar bear exhibit! A great perk for those on a budget.
After a long day of walking, you’ve now entered the relaxing portion of the day. Boka offers a great menu, and a fine bar and lounge area that sometimes offers an open seat. Make reservations in advance. If you feel you can drop $400 minimum for one (without drinks), Alinea is right next door : )
From here, it’s just a short walk down to your theater seats at the world renowned Steppenwolf Theater. This theater was founded by Hollywood stars Laurie Metcalf and Gary Sinise. It continues to put on plays that tear into your soul and leave you feeling more well rounded than when you walked in.
Marge’s Still is the perfect stop for a drink and a chance to unwind from the production you just saw. Tucked back into this neighborhood, this is one of the oldest bars in Chicago (self proclaimed longest running tavern in the city). Not even prohibition could stop this place from serving booze! With a giant beautiful mirror positioned above the bar, it’s a perfect place to relax.
The late night show at Second City is calling your name, and that’s where we’re heading next. Get to your seat a little early and to grab a drink before the show starts from one of the servers, and kick back and be prepared to laugh! These guys are professionals and usually the jumping off point for upstart comedians before they get to NY or LA.
A night cap is at the infamous Old Town Tap. A bar known for it’s grit that sits just a short ways from the Old Town nightlife that stays up probably later than you. Old Town Tap is a great spot for a beer and a story.
Day 2
After the late night last night, you’ll be ready for some grounding. And what better way to get that, than the Field Museum of Chicago.
After the World Fair back in 1893, a few locals including Marshall Field, thought it would be a good idea to house some of these relics into a museum. Later in 1930, the Field Museum was one of three main museums in the country.
Today the natural history collections includes evolutionary biolgoy, archeaology, geology, biological systematics to name a few. There’s also Sue the T-Rex. The most complete T-Rex in the world.
When you’re done admiring the artifacts, head out and north for Maggie Daley Park and soak up the sun as you walk through one the city’s newest park additions. A great park it is as it includes plenty of activities to do throughout. In the winter months, the winding path you’ll see becomes a skating rink.
Next, we’re heading west to dine at the infamous, heavy hitting Au Cheval Restaurant. There might be a bit of a wait, so head to Sawada Coffee for a little break. You might even be tempted by the delicious north Texas barbeque their sister restaurant has right next door!
After lunch at Au Cheval, you’ll want to walk around for a bit. We have the perfect place for you, in Wicker Park. Quaint botiques, vintage shops, high end shops, and plenty of food and drink options. The park itself is a perfect place to people watch or just to take a break.
Dinner belongs to Big Star. Big Star is full of character, pitchers of margaritas, high value tacos and house made salsa. And with a large patio, it’s one of the hottest places to this day in the city.
Across the street, you’ll see people lining up at a seemingly inconspicuous place. Violet Hour takes speakeast to a new level with it’s gravity stained wall having a hidden door that only opens when it has space to take more people. A great spot for a cocktail.
Don’t spend too much time down there, as The Whistler is calling your name for a show. The Whistler is a proven spot for generating local talent and having a wide array of musical talent in every night. Also, the cocktails are on point.
Next, it’s time for a night cap and dessert at Billy Sunday. Some places you just can’t replicate, and this is turning into a Chicago staple.
You’re not done yet. Get to Longman & Eagle for a late night beer. It might get busier the later it gets, but don’t be afraid. Even if you’re three back at the bar, it’ll feel like you’re enjoying the party.
That does it for Chicago. I could list plenty more (Deep dish pizza-Pequods // Italian Beef - Jhonnie’s Beef // Chicago dog - Wrigley Field bleachers you’ll find Hot Doug’s), so maybe there will be a Chicago 2! Even a Chicago 3!! And go see some jazz!!!