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August 28, 2021
Chicago, IL

Chris & Matthew

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    Things To Do

Things To Do

There's no better place to be in the summer than Chicago! Below we've listed some of our favorite spots around town, including our engagement day itinerary from August 2020.
Lakefront Trail

Lakefront Trail

Lakefront Trail, Chicago, IL

Stop #1 on our engagement day. The lakefront trail runs the entire length of the city of Chicago. Head out for a jog and get some of the best views of the lake and city. To find it, just go east until you hit water ;)

Farm Bar

Farm Bar

1300 West Wellington Avenue, Chicago, IL 60657
, (773) 281-2599

Stop #2 on our engagement day. Don't be fooled by the neighborhoody vibe. This place has incredible farm-to-table food and some of the best cocktails in the city. Be sure and ask the bartenders for a recommendation... they always seem to know exactly what you want.

Urban Kayaks on the Lakefront

Urban Kayaks on the Lakefront

110 North Lake Shore Drive, Chicago, IL 60601
, (312) 965-0035

Stop #3 on our engagement day. Get out on the water for some leisurely paddling and amazing city views. They also have a location on the river. Reservations recommended!

Crosby's Kitchen

Crosby's Kitchen

3455 North Southport Avenue, Chicago, IL 60657
, (773) 883-2525

Stop #4 on our engagement day. Stylish spot for upscale comfort food with a nice outdoor dining space, located in the popular Southport corridor among many other great restaurants and bars.

The J. Parker

The J. Parker

1816 North Clark Street, Chicago, IL 60614
, (312) 254-4747

Stop #5 on our engagement day, and also the location of our first date! Head to this chic rooftop overlooking Lincoln Park for fancy drinks and great views.

Tiny Tapp & Café

Tiny Tapp & Café

55 W. Riverwalk South, Chicago, IL 60601
, (773) 967-0102

One of our favorite summer hangout spots is the Riverwalk in downtown Chicago. Tiny Tapp hosts a preppy happy hour crowd lounging around the yachts tied up along the waterfront. Don't forget to try one of their famous frozen cocktails! For a more laid back vibe, head east along the riverwalk until you find the tiki-themed Island Party Hut.

Begyle Brewing

Begyle Brewing

1800 West Cuyler Avenue, Chicago, IL 60613
, (773) 661-6963

The craft brewery scene is booming in Chicago. There are at least half a dozen breweries we visit regularly, but many more around the city offer great beers and a laid back vibe. Begyle is our favorite. Matt is partial to the Free Bird IPA, while Chris prefers the Blonde (in more ways than one). Pro tip: There's a single skeeball machine hidden in a secret corner of the brewery!

Lincoln Park Zoo

Lincoln Park Zoo

2001 North Clark Street, Chicago, IL 60614
, (312) 742-2000

Looking for family fun? Lincoln Park Zoo is located along the lakefront a few miles north of downtown and is free for everyone. They have beautiful grounds and great animal exhibits. Highly recommended on a nice day!

Las Fuentes Restaurant

Las Fuentes Restaurant

2558 North Halsted Street, Chicago, IL 60614
, (773) 935-2004

Summer is patio season in Chicago. And if you're looking for a lively atmosphere where the margaritas are poured by the pitcher, look no further than Las Fuentes. The inside is likely to be empty, but that's because the party is outside on their massive, recently renovated patio. Ask for Daniel, the owner's son, and tell him you're in town for Chris and Matt's wedding... he'll probably give you free shots of tequila.

Chicago Architecture Center

Chicago Architecture Center

111 East Wacker Drive, Chicago, IL 60601
, (312) 922-8687

After the infamous Chicago fire of 1871, the city was rebuilt bigger and better by some of the most notable architects in history. Check out a scale model of the entire city and replicas of the world's tallest buildings in the brand new Architecture Center. If it's a nice day, reserve a spot on one of their popular river boat tours and cruise up and down the skyscraper canyon.

Museum Campus

Museum Campus

337 East Randolph St, Chicago, IL 60601
, (312) 742-7529

Chicago has some of the best museums in the world, and three of them are within walking distance of each other. The Field Museum is a massive hall of natural history. The Shedd, one of our personal favorites, is an aquarium with sharks, whales, and a dolphin show. The Adler Planetarium has some great space exhibits. The museum campus also has some of the best views of the Chicago skyline.

Wrigley Field

Wrigley Field

1060 West Addison Street, Chicago, IL 60613
, (773) 404-2827

We've spent many fun summer afternoons in the friendly confines of Wrigley Field, which opens for tours of the historic ballpark. But if you're looking for the Cubs in action, they'll be on the south side playing the White Sox in the cross-town classic!

For all the days along the way
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