Chicago: A Perfect City Weekend Getaway

October 05, 2018

Chicago: A Perfect City Weekend Getaway

Chicago, The Windy City

Chicago is a huge city with a lot to do, but it can also be a very peaceful relaxing city. Whether you are looking to relax or explore, Chicago is sure to have a few things for you and be a perfect weekend getaway.



Where to Stay:

Picture Perfect Pied-à-terre on the North Side

 house chicago

Why we like it: This Airbnb truly is picture perfect. Though it is about 15 – 20 minutes from most of the things on this guide, the price and design makes it totally worthwhile. So what are you waiting for? Book a weekend, order your Weekend Getaway Candles (link to weekend getaway), and let’s start planning a Chicago weekend getaway!



Friday Night

Deep Dish Pizza $12/person

 deep dish pizza chicago

👍 Why we like it: Deep dish Chicago style pizza is an essential when in the windy city. The cheese and tomato sauce is piled high for an ultra thick incredible pizza that you will be craving.  It’s an age-old debate as to who does it best and we don’t want to get in the middle of it. So take your pick. This article might help you decide which pizza shop to visit.

🍽 What we order: All the deep dish




Ipsento 606 $7/person


👍 Why we like it: We love Ipsento for their quality coffee, delicious baby doughnuts, and the perfect location. Located just off the 606, Ipsento is the perfect place to grab some coffee and take a stroll. (Which is just what we recommend)

🍽 What we order: coffee and 1 or 2 baby doughnuts


Ride, Walk or Run the 606

 the 606 chicago

👍 Why we like it: It really doesn’t get better than the 606 in autumn. Formerly an elevated railroad track, the 606 is now a three-mile greenway. The 606 is the perfect way to enjoy a few of Chicago’s neighborhoods and a little nature at the same time.


Bang Bang Pie & Biscuits $15/person

 bang bang pie and biscuits chicago

👍Why we like it: Everything on the menu is delicious (and the hot sauce is equally so). Don’t let the long line turn you off, wait 15 – 20 minutes and then grab a seat in the beautiful outdoor seating area - good food awaits. 

🍽 What we order: the pimento biscuit, candied bacon, A bottle of hot sauce to take home. 


Explore Wicker Park

 wicker park chicago

👍 Why we like it: Given the choice between downtown Chicago and a smaller Chicago neighborhood, we pick the neighborhood every time. The trendy Wicker Park neighborhood has everything we want: great local shops, delicious food, trendy bars, residential areas, and lots of people watching.


Visit a Museum + a Park  $40/person

 chicago museum and park cloud gate sculpture sue

👍 Why we like it: There are plenty of world-class museums in Chicago and many of them are located in the same area as many world-class parks. Why not hit both?

🏞 Parks: Millennium Park, Maggie Daley Park, Grant Park

🏛 Museums: Shedd Aquarium, The Field Museum, Adler Planetarium, The Art Institute Chicago 


Green Street Smoked Meats  $25/ person

 green street smoked meats

👍 Why we like it: Texas style BBQ in the middle of Chicago –and it’s good. Set in an old Chicago warehouse and dimly lit by string lights, Green Street Smoked Meats is one of our all around favorite BBQ joints. To make matters better, it is attached to Sawada Coffee. If you aren’t too stuffed after your food, slip over to Sawada and grab a boozy steamer. 

🍽 What we order: sliced brisket, baked beans, macaroni salad



Allis at Soho House $12/ person

 the allis chicago

👍 Why we like it: The Allis is one of the dreamiest places we could imagine: Concrete walls and industrial windows, juxtaposed by velvet couches, antique chandeliers, and old woods. Sit down and enjoy the full service coffee bar.

🍽 What we order: cappuccino, a baked good


River Tour $50/ person

river tour chicago

👍 Why we like it: The best way to see downtown Chicago is from the river. Weave in and out of the city’s skyscrapers by boat as a tour guide tells about the architecture and history of each building.


Small Cheval  $15/person

 small cheval chicago

👍 Why we like it: It’s not complicated what makes Small Cheval really good – its just a great burger and fries. Be sure to order the burger house style, because they have perfected it. Make your way to the condiment station and get some garlic aioli for the fries, and find a seat outside.

🍽 What we order: Cheeseburger (house style), fries with garlic aioli


Walk Along Lake Michigan

 lake michigan chicago          

👍 Why we like it: Walking along lake Michigan brings two worlds together for beautiful views all around. On one side you have a vast lake, more accurately described as a small sea. On the other side there is a massive and busy city.


Shop Michigan Ave

 michigan ave chicago      

👍 Why we like it: One of America’s most popular shopping districts, The Magnificent Mile is home to many of retails most popular names. No matter what your budget, you are sure to find a store to shop at: from Forever 21 to Louis Vuitton, Michigan Avenue’s Magnificent Mile has it all.


Velvet Taco $18/person

 velvet taco chicago

👍 Why we like it: We never turn down a trendy taco shop and Velvet Taco certainly didn’t disappoint. The unique tacos, delicious margaritas, craft sodas, and edgy space make for a perfect casual but satisfying dinner.

🍽 What we order: Spicy tikka chicken taco, annatto shredded pork taco, grilled flank steak taco, margarita or craft soda

Recommended For You: 

🌴Charleston, SC Travel Guide

Asheville, NC Travel Guide

🛍Shop Weekend Getaway

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