Things To DoThings To Do

The 606The 606

One of our favorite Saturday activities is taking a bike ride or walk along the 606 (or the Bloomingdale trail). There are Divvy bike rentals at multiple points along the trail. You can hop off the trail at different streets and check out Wicker Park, Bucktown, Logan Square and Humboldt Park! All have great food and drink options :)

Lakefront Trail - Grant ParkLakefront Trail - Grant Park

You can get to this trail at multiple points but its a great place to grab a bike and go for a ride or long walk and see Lake Michigan! The beaches are free, so take a dip while your at it!

Chicago RiverwalkChicago Riverwalk

Tons of fun restaurants and bars to stop at - a great place for an evening (or early morning) stroll - or I suppose if you're ambitious, a run.

Chicago River Boat Architecture ToursChicago River Boat Architecture Tours

This is an amazing river tour of all the cool Chicago architecture and a really fun excursion for Saturday or Sunday morning! Book your tickets ahead of time, in the summer they fill up fast!

Field MuseumField Museum

The Art Institute of ChicagoThe Art Institute of Chicago

White Sox Game!White Sox Game!

Needless to say- we are White Sox fans in this household. Check out a game while you're in town!

Avondale BowlAvondale Bowl

Feel like lacing up your bowling shoes - check out Avondale Bowl - make sure to book your lanes in advance though - this place is very popular!

Big Mini Putt ClubBig Mini Putt Club

Cassie has definitely lost more than one round of mini golf to Dan here... but it's always fun!

The Second CityThe Second City

Check out some great comedy shows here!

Elina'sElina's

Probably one of our top 2-3 favorite Italian restaurants in Chicago - you definitely need a reservation here, but if you are looking for some good food Friday night - this is the spot!

Parson's Chicken & FishParson's Chicken & Fish

There are three Parson's locations - this one is accessible off the 606 - but if you want some good fried chicken - this is your spot.

UnionUnion

This was our first date spot - the burger is great, the fried olives are even better. Wander next door to Lardon for some wine and charcuterie or around the back to Meadowlark - a very fun speakeasy!

SegnatoreSegnatore

Another one of our favorite Italian spots and our engagement dinner spot! Also has great brunch.

KasamaKasama

Here is the move- order this brunch to go (you will never get in for breakfast) and then take it to a park nearby or to the lake front or the 606 and enjoy some bomb brunch food in a beautiful spot.

The LoyalistThe Loyalist

If you want a great burger, chocolate chip cookie and a martini- this is your spot. Its our fave burger spot for sure. And we tend to be burger snobs...

Lula CafeLula Cafe

You need a good brunch - this is your spot. (or at least a good option)

Longman & EagleLongman & Eagle

Best Chicken and Waffles ever. (in Cassie's opinion at least)

Bungalow by Middle BrowBungalow by Middle Brow

Great wine, pizza and beer - what more do you need??

Taqueria ChingónTaqueria Chingón

If you need great tacos and amazing churros - this is the place to go.

BoeufhausBoeufhaus

Short rib beignets?? DO we need to say more?

Time Out Market ChicagoTime Out Market Chicago

Large food hall with multiple options from some great Chicago restaurants. A good option if you dont want the hassle of a reservation and arent sure what you want to try yet!

D'Amato's BakeryD'Amato's Bakery

The source of the best cannoli, focaccia, and Italian cookies in the city

Rhine Hall DistilleryRhine Hall Distillery

We have done cocktail classes here several times - we love this distillery which specializes in brandy, they make great cocktails! Not to mention, they are right down the street from Goose Island.

ScofflawScofflaw

Definitely one of our favorite bars in this city - they make a stiff drink, and some great food. Also close to Outside Voices - a great little wine bar AND Best Intentions- quite the fun dive if you are looking for it.

EstereoEstereo

This was supposed to be our first date but ended up being our 3rd or 4th - its a great spot for some delicious cocktails, but beware, they are stronger than you think. There's also a Fulton Market location, but this one's our favorite.

Tack RoomTack Room

While one of our favorite spots - Dusek's is closed, Tack Room and Punch House are still open! They are great places to grab a drink or sing along with the piano!

The Hi-LoThe Hi-Lo

Great drinks, fun vibe - right down the street from Segnatore

Little VictoriesLittle Victories

SUNNYGUNSUNNYGUN

Nice patio spot for drinks

The Aberdeen TapThe Aberdeen Tap

Great patio spot for drinks!

Best IntentionsBest Intentions

The Green Door TavernThe Green Door Tavern

A pretty standard bar with a very fun burlesque style speakeasy in the basement. Definitely worth it.

CiraCira

The lobby bar of the Hoxton - a good spot to grab a happy hour cocktail.

Lazy BirdLazy Bird

In the basement of the Hoxton, our second date spot :)

Good FunkGood Funk

Nice little wine bar with some funky natural wines along the river!

TRUCETRUCE

One of our new favorite cocktail spots. Pretty amazing espresso martinis and doubles as a great coffee shop during the day.

Guinness Open Gate Brewery – West LoopGuinness Open Gate Brewery – West Loop

The new Guinness Tap Room if beer (and specifically Guinness) is your thing!

Goose Island TaproomGoose Island Taproom

Fun Chicago brewery (although there are a ton of others on the list to check out that are lesser known!)

Revolution Brewing - Brewery & TaproomRevolution Brewing - Brewery & Taproom

Begyle BrewingBegyle Brewing

Hopewell Brewing CompanyHopewell Brewing Company

Dovetail BreweryDovetail Brewery

Maplewood Brewery & DistilleryMaplewood Brewery & Distillery

Marz Community Brewing CompanyMarz Community Brewing Company

Will's Northwoods InnWill's Northwoods Inn

Can't have Dan's wedding website without Will's on here. Step into Wisconsin in this bar up in Lakeview. Just don't sit on the moose