The Shedd Aquarium – “We had one of our favorite date days here and even fed the belugas!”

Lincoln Park Zoo – “We once spent an afternoon here laughing as the polar bears swam and showed off in the pool.”

Architecture Boat Tour – “We recommend this to everyone—it’s iconic Chicago and we’ve done it ourselves!”

Other Chicago Classics:

Millennium Park & The Bean

The Art Institute of Chicago

Skydeck Chicago (Sears Tower) or 360 CHICAGO (John Hancock)

Museum Campus (Field Museum, Adler Planetarium)

Walk or bike the Lakefront Trail

Chicago Classics: Deep-dish pizza (Lou Malnati’s, Pequod's), Chicago dogs, Italian beef

Our Go-To Date Night Restaurants:

La Scarola: You cannot visit Chicago and not stop here. This is hands down the best Italian food in the city. We both recommend the cheese ravioli.

Mercadito: Our go-to for Mexican date nights—fun vibe, amazing tacos, and some of the best guac in the city. We never skip it.

Bub City: Low-key, country vibes and seriously good food. We’d go for the hot & spicy chicken sandwiches or burgers, and Megan always had to get the fried pickles.

Lincoln Park Neighborhood Gems:

Chicago Pizza & Oven Grinder: A one-of-a-kind dining experience you won’t find anywhere else—they invented the pizza pot pie, and it’s as indulgent as it sounds.

Cafe Ba-Ba-Reeba!: Chicago’s original tapas bar, serving authentic Spanish small plates and top-notch sangria since 1985. A lively spot for sharing bites and catching up.

Peaquads Pizza: Famous for its caramelized cheese crust and thick, doughy slices—often ranked among Chicago’s best deep dish. Be ready to wait, but it’s worth it.

R.J. Grunts: A perfect pitstop after a visit to the Lincoln Park Zoo. Great burgers, an old-school salad bar, and don’t skip the milkshake—you're on vacation, after all.

Best Places for a Nightcap or Cocktail: If you're in the mood for a great drink with a view—or something a little more unexpected—Chicago delivers.

Cindy’s and LondonHouse both have stunning rooftop bars—perfect for sunset cocktails or a post-dinner nightcap.

The J. Parker at Hotel Lincoln (where our wedding room block is!) has one of the best skyline views in the city—grab a drink and soak it in.

Three Dots and a Dash – A hidden tiki bar in River North serving over-the-top rum cocktails in a tropical, underground setting. It’s a fun surprise once you find the alley entrance.

The Violet Hour – A speakeasy-style cocktail bar in Wicker Park with craft drinks, candlelight, and a hidden front door (just look for the ever-changing mural).

The Berkshire Room – A moody, stylish spot tucked inside the ACME Hotel in River North—perfect for a more low-key, elevated nightcap.

Live Music & Comedy:

Second City (a must if you like to laugh)

Green Mill Cocktail Lounge (jazz and Al Capone history)

Lollapalooza

Chicago Sports:

Catch a Cubs or Sox game

Visit the United Center for Bulls Game

Head to Soldier Field to see the Bears or Chicago Fire

Unique Activities:

Enjoy Lake Michigan: head to the beach or rent a kayak to take out into the water

Board a Boat at Navy Pier: Whether it’s a sunset cruise, lakefront party boat, or a fireworks cruise on summer nights, hopping on a boat from Navy Pier is always a good time.

Art on theMART: Watch massive digital art projections light up the side of the Merchandise Mart after sunset. It’s totally free and a cool way to end the night along the riverwalk.

Chicago is a big city, but getting around is easier than you might think.

The ‘L’ Train: Don’t be afraid of the 'L'—it’s how locals get around! It's affordable, convenient, and a great way to see the city from above.

Ride Shares & Taxis: Uber and Lyft are widely available, especially downtown and near popular attractions.

Walking: Chicago is a very walkable city, especially in neighborhoods like Lincoln Park, the Loop, and River North. Just make sure to pack comfy shoes!

Divvy Bikes & Scooters: For a more adventurous route, hop on a Divvy bike or electric scooter—great for exploring the lakefront or nearby parks.

Pro tip: If you're staying a few days, consider getting a Ventra card to make taking the train or bus even easier.

Chicago Deep Dish Pizza

Will’s Pick: Lou Malnati’s – “That buttery crust is unbeatable.”

Megan’s Pick: Pequod’s – “Give me the caramelized cheese crust any day.”

Chicago Pizza (Yes we have pizza that's not Deep Dish)

Will's Pick: Roots - "Quad City style is the closest to a New York slice you can find in the Midwest."

Megan's Pick: Flo & Santo's - "Thin and crispy! Contrary to what Will say's its not a cracker with some sauce and cheese."

Chicago-Style Hot Dogs

Will’s Pick: Devil Dogs – “It’s a classic, and they don’t mess it up.”

Megan’s Pick: Weiners Circle– "Okay, confession: I don’t eat hot dogs—but if I did, I’d send you straight to Wieners Circle. Get one with the chocolate shake… if you know, you know 😉"

Italian Beef Sandwiches

Will’s Pick: Portillo’s - "get it with the Chicago pepper stuff!" "(it’s pronounced ‘jar-din-air’ (giardiniera)!” - Megan

Megan’s Pick: Pops – “It has to be dipped, with a side of cheese fries."

Best Burger in the City

Will’s Pick: White Palace Diner - "Everybody from Jersey knows that diners have the best burgers!"

Megan’s Pick: Au Cheval – “Yes, it’s worth the hype.”

Top Steak House

Will's Pick: Chicago Cut Steakhouse – “This was the go-to spot for celebrating big wins—nothing marked a commission check quite like a steak dinner with the guys. A classic Chicago power move.”

Megan's Pick: Bavette's Bar & Boeuf - "One of my first splurge dinners after I started working in the city—I had to share a filet with two co-workers, and it was worth every penny. I still smile every time I walk past it.”