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take a summer weekend getaway to Chicago

Aug 9, 2019

Exploring Downtown at 28 Weeks Pregnant

Hey hey friends,

So, I may be a little biased, but clearly, I love Chicago. And even more so, I love Chicago in the summertime. Whether you want to day drink on a patio, chill at the beach, or venture around the city, the options are unlimited. I wanted to share what I consider the ideal weekend plans, that would make the perfect girl’s weekend, couple’s getaway, or babymoon!

View from the Centennial Wheel on Navy Pier at Sunset
Brussel Shuffle pizza at Parlor Pizza

First, you have to grab a delicous dinner and drink Friday night. If you’re in the downtown area, I would suggest somewhere in River North, like Public House (can you say boozy cake shakes?), Parlor Pizza (Brussel Sprout pizza mmm…) or get a little fancier at Siena Tavern.

Half-Pound Pizza Pot Pie at Chicago Pizza & Oven Grinder Co.

If you are a tad further north, DEFINITELY check out Chicago Pizza & Oven Grinder Co. It is a little hole in the wall joint that one may recognize from their one-of-a-kind Pizza Pot Pies that have been featured on Food Network vids floating around Facebook. They are almost always busy and do not take reservations, but IT IS WORTH IT. Get the Mediterranean bread as a starter and a 1/2 pound Pizza Pot Pie. They are a cash-only place, but have valet parking and are open until 11pm on the weekend. Then, if you aren’t too stuffed, go out for drinks at a hot spot like Joy District, Fremont, or get your hula on at Three Dots and a Dash.

Buckingham Fountain

Saturday, don’t sleep in too late, but it is a mini-cay after all… so after a couple of snoozes, get ready for some bomb brunch. Brunch is a staple of any great Saturday in Chicago. Whether you’re near their downtown or the north side locations, I can’t recommend Hutch enough. When we lived in Wrigleyville, we went to Hutch American Bistro a couple of times a month. They have delish mimosas (try White Peach!) and specialty drinks with their own house-infused pineapple or jalapeno vodka. My favorite is definitely the Bistro Sandwich. Otherwise, you should check out somewhere in River North like Beatrix or Pops for Champagne.

Once you’ve brunched it up, you need to walk over to Millenium or Grant Park for some site-seeing (the BEAN & Buckingham Fountain) and Michigan Ave. for some shopping! When you’re ready to relax, head over to the River Walk along the Chicago River and find a spot at one of the riverside restaurants, like City Winery, and grab yourself a cocktail and a little afternoon snack. If you’re still feeling up for more site-seeing, I HIGHLY recommend an architecture boat tour. You can just sit back, grab a drink, and relax while learning about the cities amazing history. We took one on 4th of July weekend and it was amazing.

Downtown at Millennium Park
Bellemore’s Smokin’ Berries Cocktail

If you want something a bit fancier, jump over to the West Loop and check out Bellemore. Decadent cocktails, creative courses, and fantastic dessert. Both times I’ve been, the menu has been changed to feature new items, but if there is something with foie gras involved, GET THAT. We had an amazing dish that featured a frozen shaved foie gras with berries that just melted in your mouth. YUM. Also, get the Hawaiian Rolls as a starter. You’ll thank me later. 10/10 all around. After dinner, try to take in a show at one of the many performance theaters downtown or just head down to Navy Pier for a walk around the pier and the firework show that can be been all summer on the weekends after sunset (MUST SEE).

Navy Pier Summer Firework Display

Before you head out in the morning, make sure to pop in for a coffee and pastry somewhere like Goddess and the Baker, Firecakes Donuts (try the Blueberry Lemon cake if it’s in season or the Wildflower Honey Glazed!) or Intelligentsia Coffee.

You can’t go wrong trying any of these places. You’ll see and eat the best of Chicago on the perfect summer getaway! Is there a spot in Chi you highly recommend? Drop your favorites in the comments! Enjoy Chicago, lovelies!

xx, the windy city mama

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