First Time Visitors Itinerary Opinion - Friday to Wednesday

Question

Hi All,

My wife and son who's 7 are visiting Chicago for the first time next week and can't wait!

I've put together a rough itinerary and would appreciate if anyone who has time to have a quick look to see what they think? We want to make the most out of our visit but without rushing around everywhere.

FRIDAY

We land in the afternoon and will arrive at the hotel around 3-4 p.m. Staying downtown at the Royal Sonesta. Haven't booked transfers yet but looking into it.

> Millenium Park Tree Lighting Ceremony at 7 p.m.

> Meal at Lou Malnetti's to try proper Deep Dish

SATURDAY

Breakfast at Wildberry Pancakes or wherever

Mid to late morning > Architecture Boat Tour

Afternoon Chriskindle Market and the other festive activities in the area that's going on before finding somewhere to stand for the Parade then watch the fireworks from the bridge if it's easily walkable through the crowds.

Maybe some food back at the hotel or somewhere after the Parade & Fireworks.

SUNDAY

Breakfast somewhere then an Uber or Public Transport over to Soldier Field to my beloved Bears against Vikings (got tickets and hoping it won't be a painful watch given their last 3 games). Contemplating going to a tailgate event before the game but not sure yet and whether it's something my 7 year old would enjoy?

After the game >> Walk over to visit Shed Aquarium for a few hours then we've booked for 7:30 p.m. to see the Christmas Lights at Lincoln Park Zoo so we'll get an Uber or something from the Aquarium to Lincoln Park.

MONDAY

More relaxing day. Shopping Miracle Mile. Water Tower Place. Nike store etc.

Meal at Cheesecake Factory then visit 360 at sunset (will book in advance tickets).

Afternoon from 360 Uber over to Navy Pier and ride the wheel etc.

TUESDAY

If we can get in a meal at Macy's Walnut Room whether it's Breakfast or Lunch. Shopping at Macy's and explore that area.

Evening - Possibly see Christmas Carol at Goodman Theatre.

WEDNESDAY -

Breakfast somewhere then a little shopping before heading to airport around lunchtime.

The only things I've left out are riding the Holiday Train that would be great to do and also possibly seeing the Home Alone House in Winnetka. My wfie and son aren't bothered about seeing the house but I am, so may get an Uber there and back on one of the days on my own to see it and capture some pics.

Any other MUST DO's, especially during this festive time that we may have missed I'm all ears. Whether it be certain restaurants to visit or something else.

Many thanks in advance!

Answer

Your itinerary looks great! It's packed with fun activities without being overly rushed, and you've really planned for some key Chicago experiences. Below are some thoughts and additional suggestions for your trip:

FRIDAY

The Millenium Park Tree Lighting Ceremony sounds like a perfect way to kick off your visit, especially if you're visiting during the holiday season. Lou Malnati's is a fantastic choice for deep dish pizza, but you might want to get there early or expect a bit of a wait since it can be quite popular.

SATURDAY

Breakfast at Wildberry Pancakes is a great choice; it’s well-loved and has delicious options. The Architecture Boat Tour is one of the top Chicago activities and a great way to see the city from a different perspective. Just make sure to dress warmly since it can get chilly on the water during the winter.

The Christkindlmarket is a festive experience for the whole family, especially if you enjoy browsing for holiday gifts, drinking hot chocolate, or simply soaking in the festive atmosphere. The Parade and fireworks will be a fun way to cap off the day, but since it’s crowded, be prepared to navigate through some crowds. It may also be difficult to get close to a good viewing spot on the bridge, so plan ahead.

SUNDAY

Heading to Soldier Field for the Bears game is a fantastic experience, especially if you're a fan! Whether or not to go to a tailgate event depends on your son and how much he enjoys that sort of thing. Tailgating is fun, but it can get cold, and it might be a bit overwhelming for a 7-year-old. I'd suggest checking out the event from afar if he’s not too keen on the party atmosphere.

The Shedd Aquarium is always a hit with kids, and it’s right by Soldier Field, so it’s easy to do after the game. The Lincoln Park Zoo Christmas Lights are also a must-see during the holiday season and a perfect evening activity. You'll enjoy the zoo lights as it's one of the most beautiful Christmas displays in the city.

MONDAY

Shopping on the Magnificent Mile (Miracle Mile) will be a treat! Water Tower Place and the Nike Store are popular stops. The Cheesecake Factory is a good choice for a meal, but if you’re looking for something a little more local or unique, consider trying Portillo's for Chicago-style hot dogs or Giordano's for another deep-dish pizza experience.

The 360 Chicago observation deck at sunset sounds like an amazing way to take in the city views. Make sure to book your tickets in advance to avoid long lines. Afterward, a visit to Navy Pier and the Ferris Wheel is great, especially during the holidays when the Pier is decorated with lights and holiday cheer.

TUESDAY

The Walnut Room at Macy's is a Chicago institution for a holiday meal. If you’re able to get a reservation, it’s worth it. Shopping at Macy’s and exploring the State Street area is a nice way to spend part of your day. If you’re interested in theater, seeing A Christmas Carol at the Goodman Theatre is a great holiday tradition. It’s a fantastic family-friendly show if you're looking for some classic holiday entertainment.

WEDNESDAY

Your plan to shop a bit before heading to the airport sounds like a good, relaxed way to wrap up your trip. If you still have some time to spare, you might also consider checking out the Art Institute of Chicago, especially if your son is into art, as they often have family-friendly activities or exhibits.

Additional Tips & Must-Dos:

Holiday Train: If you have a bit of extra time, try to fit in a ride on the CTA Holiday Train. It’s a fun, festive experience, especially for your son, and runs on select routes during the holiday season.
Chicago Christmas Markets: In addition to the Christkindlmarket, consider visiting the other holiday markets around the city, like the one at Lincoln Park Conservatory or Chicago French Market.
Ice Skating: If the weather permits, the ice skating rink at Maggie Daley Park is another fun winter activity for the whole family.
Visit the Bean: Don’t forget to stop by Millennium Park and take a photo by the iconic Cloud Gate (aka "The Bean"). It’s a classic Chicago experience!
Home Alone House: If you’re a fan, the Home Alone house in Winnetka is worth a quick trip, but it’s a bit of a distance, so you might want to consider it as a solo trip if you’re interested in capturing photos.

Overall, your itinerary is balanced, fun, and family-friendly, with a good mix of sightseeing, shopping, holiday activities, and some downtime. Enjoy your trip, and I hope you all have an amazing time exploring Chicago!