Nicole & Rob

Nicole & Rob

May 24, 2025 • Chicago, IL
44 Days To Go!
Nicole & Rob

Nicole & Rob

May 24, 2025 • Chicago, IL
44 Days To Go!

Things to Do

Some of our favorite lunch spots

Au Cheval

800 W Randolph St, Chicago, IL 60607, USA
(312) 929-4580

The best burger you can get. They don't take reservations, get there and put your name down.

Website

Frontera Grill

445 N Clark St, Chicago, IL 60654, USA
(312) 661-1434

Rick Bayless is such a Chicago legend the city gave him a day! The best Mexican chef in Chicago. This spot is great for lunch.

Little Goat Diner

3325 N Southport Ave, Chicago, IL 60657, USA
(773) 819-7673

A diner brought into the modern era by the icon Stephanie Izzard. Literally everything there is delicious.

Athenian Room

807 W Webster Ave, Chicago, IL 60614, USA
(773) 348-5155

Great Greek spot, the chicken is beloved. Rob also gets the burger there.

Aba

302 N Green St 3rd Floor, Chicago, IL 60607, USA
(773) 645-1400

Israeli staple.

Pequod's Pizza

2207 N Clybourn Ave, Chicago, IL 60614, USA
(773) 327-1512

Nicole's favorite Detroit Style pizza. Controversial take, many call it Chicago style.

Lou Malnati's Pizzeria

410 N Michigan Ave, Chicago, IL 60611, USA
(312) 858-5600

Our favorite deep dish place! Head's up that deep dish takes 45 mins to make. Our go to is thin crust Pepperoni and mushroom. PRO TIP: ask for it well baked.

Al's #1 Italian Beef

548 N Wells St, Chicago, IL 60654, USA
(312) 943-3222

The best Italian Beef option in all of Chi-Town. Plan in advance may be a line.

Portillo's & Barnelli's Chicago

100 W Ontario St, Chicago, IL 60610, USA
(312) 587-8910

Chicago Dog classic option

Day Activities

The MUST

Chicago River Boat Architecture Tours

465 N McClurg Ct, Chicago, IL 60611, USA
(708) 488-6343

This iconic tourist activity is so much fun the locals love it! There are several competitors with a few launch points. Plan in advance and get a tickets! There are various lengths to choose from.

America's Pastime

Wrigley Field Tour

1060 W Addison St, Chicago, IL 60613, USA
(773) 404-2827

The Cubs chose to give the weekend to us, which means their iconic home is wide open! There are tours open to the public on Saturday and Sunday.

Texas Rangers @ Chicago White Sox

333 W 35th St, Chicago, IL 60616, USA
(312) 674-1000

The Texas Rangers are in town for the weekend to face off against the Chicago White Sox. Fair warning last season the White Sox were the worst baseball team of the last 120 years.

Seeing the city on your feet

Walk Around Downtown Chicago

201 E Randolph St, Chicago, IL 60602, USA

May in Chicago is the perfect time to walk around downtown and soak in one of America's best cities. The address here is at the Bean. Enjoy a jaunt through Millennium Park and the River Walk!

Lake Michigan

1603 N Jean Baptiste Pointe du Sable Lake Shore Dr, Chicago, IL 60611, USA
(312) 852-9258

No better way to enjoy summer in Chicago that soaking in Lake Michigan. The location is set to a kayak rental. You could also find a boat or simply walk along the coast.

Museums

Field Museum

1400 S Lake Shore Dr, Chicago, IL 60605, USA
(312) 922-9410

The largest and most complete Tyrannosaurus Rex Skeleton ever discovered is on display, need I say more?

Adler Planetarium

1300 S Lake Shore Dr, Chicago, IL 60605, USA
(312) 922-7827

A favorite of Nicole's since childhood. A great escape to see what's beyond.

The Art Institute of Chicago

111 S Michigan Ave, Chicago, IL 60603, USA
(312) 443-3600

If Ferris Bueller had to take a day off to go the Art Institute maybe you should too! Put Twist and Shout on your airpods while you gaze at a Starry Night or a Sunday on La Grande Jatte.

Griffin Museum of Science and Industry

5700 S Lake Shore Dr, Chicago, IL 60637, USA
(773) 684-1414

What is better than enjoying a demonstration of American Ingenuity? The answer, not much. Maybe a wedding.

Pay to Play

Skydeck Chicago

233 S Wacker Dr, Chicago, IL 60606, USA
(312) 875-9447

We call it the Sears Tower. If you want to be at the highest point in the city and gaze down upon us, head on up to the Skydeck at the Willis Tower.

The Second City Training Center

1608 N Wells St f4, Chicago, IL 60614, USA
(312) 664-3959

The most successful comedy institution not in LA or NYC is right here in the windy city. There's a sketch show at 3:00 on Saturday if you want to get a laugh on.

Play

Chicago has a thriving theatre scene, a great opportunity to see performers on stage at a matinee!