The Perfect West Loop Weekend

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Amit Thakral

The West Loop neighborhood is currently the hottest Chicago destination for dining, nightlife, shopping, and more. From Willis Tower to niche food spots, there is an endless amount of things to do. Here’s how we’d spend the perfect weekend in the West Loop.

Day 1

Start your weekend off right with breakfast/brunch at Yolk. Located in Ogilvie Transportation Center, Yolk is a convenient option for those coming into the city through Ogilvie or Union Station. Fuel up for the weekend with Yolk’s own private label premium coffee, specialty juices, and creative breakfasts. 

After breakfast, you’re only ten minutes away from the Willis Tower, where you can experience the best views in the city from the Skydeck. If you’re feeling brave, you can stand on “The Ledge,” a glass-floored balcony extending outside of Willis Tower’s 103rd floor. You can also dine above the clouds with Skydeck’s exclusive dining options.     

A short five-minute drive or fifteen-minute walk will bring you to Greektown, a historic neighborhood brimming with restaurants and entertainment. Check out the National Hellenic Museum for an inside look at Greek heritage and culture in Chicago. Then, grab a bite at Greek Islands, dubbed “The Best Greek Restaurant in Chicagoland.” With a comprehensive wine list and family style options, it’s a great choice for those looking for an authentic experience. 

End your night with cocktails at Selva, located inside The Emily Hotel in the Fulton Market District. The perfect place for both dining and lodging, The Emily Hotel features multiple restaurants, rooftop movie screenings, and all-encompassing amenities. The best part? After your nightcap, you’re only an elevator ride away from a restful night’s sleep.  

Day 2

After a quick pick-me-up from The Emily Hotel’s coffee bar, immerse yourself in art at the WNDR Museum on Monroe Street. Designed to boost curiosity, creativity, and community, WNDR offers awe-inspiring interactive art, a lounge, and shop. With over 21 art installations, there is a unique experience for everyone. 

Feeling peckish after WNDR? The McDonald’s Global Menu Restaurant is a casual and convenient lunch option, and you can walk there in under 10 minutes! Experience international fast food right in Chicago, with items like the Philly Cheese Stack from the United Kingdom, McSpicy BLT from Malaysia, and the Biscoff McFlurry from Belgium. For a local/Irish inspired dessert, head to Cone Gourmet Ice Cream on Madison.

The West Loop prides itself on local shops and businesses, and you’re right near them all. Spend your afternoon shopping for locally made apparel and goods at withlove collective, find your next great read at Madison Street Books, or discover sustainable alternatives for everyday items at The Unwaste Shop. Other great shops include:

When dinner time rolls around, head over to Saigon Sisters, Chicago’s best-rated Vietnamese Restaurant. Owned by sisters Mary Nguyen Aregoni, Theresa Nguyen, and their mother, Mama Suu, Saigon Sisters combines authentic Vietnamese and French cuisine to create a curated culinary experience. Their most famous dishes include Pho, Banh Mi, Baos, and more. Seating is limited, so making a reservation is highly recommended. If you want

Day 3

Next, spend your last day in the city by getting your adrenaline pumping at Brooklyn Boulders. Their multi-level facility houses a large variety of climbing to suit your experience level. With a day pass, you get full access to climbing and fitness facilities, locker access, towel service, and group fitness classes. 

To close out the weekend, stop by the Chicago French Market and get some treats for the trip home. Located inside Ogilvie and minutes away from Union Station, it’s a super convenient spot to visit right before you leave. The market is open year-round, and features over 20 local vendors including Mochii Donut and Dogs, Bon Appetit Creperie, and Suarez Market. With so many options to choose from, visiting the French Market is the perfect way to sample authentic Chicago cuisine one last time. 

Why the West Loop is Called the ‘Best Loop’

The West Loop has it all, from jaw-dropping views to one-of-a-kind culinary experiences. Here, you can visit cultural landmarks, shop ‘til you drop, and enjoy award-winning cuisines without leaving the neighborhood. The West Loop is waiting for you! 

For more inspiration, check the brand new Chicago Does Neighborhood Map of the Near West Side!