I’m heading to Chicago with two of my kids this month (using miles and points), and we cannot wait! I haven’t been to Chicago in 28 years, and I’m sure a lot has changed.
For those who live in the area or anyone who has visited recently, I’d love some suggestions on your favorite things to do. My kids are 13 and 16. Here is what I have so far:
Chicago Itinerary
Day 1:
We land at O’Hare around 2:30 p.m. We will be packing carry-ons and plan to Uber to the Hyatt Regency Chicago.
- Walk to Millennium Park to see Cloud Gate (aka The Bean) before it gets dark. It’s about 10 minutes from our hotel
- Take Uber to Greek Town for dinner (any suggestions?)
Day 2:
- Go to the Skydeck at Willis Tower (late morning/early afternoon) or 360Chicago
- See Blue Man Group Show in late afternoon (I already have tickets)
Day 3:
- Wide open! Ideas: Lincoln Park Zoo lights, Shedd Aquarium, the Christkindlmarket (German Christmas market), river or lake cruise, Centennial Wheel at Navy Pier
Day 4:
- We have no plans until noon, when we head to Union Station to catch the train back to Dallas
What do you recommend?
Author: Nancy
Nancy lives near Dallas, Texas, with her husband and three kids. Her favorite vacations include the beach, cruising and everything Disney.
It was 32 degrees and snow covered the grass and rooftops yesterday morning (Nov 1st)! I was just reading about the Chicago underground pedway yesterday. Looked interesting – might be good if weather is bad outside. I was thinking of taking the Southshore to Chicago and found a site with step by step instructions of taking the train and bus to Ohare. I read the blue line goes right to Ohare, although I see an alert that the elevator at O’Hare is temporarily down. Sites I bookmarked for more info;
https://www.chicago.gov/city/en/depts/cdot/provdrs/ped/svcs/pedway.html
https://www.youtube.com/watch?v=dHR_lkwTBRA video walking tour of pedway
https://laportecounty.life/article/south-shore-line-provides-easy-access-to-chicago-ohare-and-midway-airports/
https://www.transitchicago.com/airports/
https://www.transitchicago.com/maps/ – downtown sightseeing map
https://www.transitchicago.com/destinations/#arts
Thank you, Cari!
You’re taking a train back to Dallas? Interesting.
@Christian Yes, we took Amtrak from San Francisco to Denver when the kids were younger and they’ve been begging to do an overnight train trip again. So, I figured this Chicago to Dallas route is our chance. Unfortunately, my oldest son will still be at college and will miss out.
My teenage sons enjoyed the Art Institute Chicago on Michigan Ave..
Loved the Chicago Architecture boat tour through the canals. Excellent narration. Got on the boat — not far from the Hyatt Regency.
Museum of Science and Industry (hands on; great for science geeks)
German Food: Berghoff (old standard)
Breakfast: Yolk (chain in Dallas now too but based up there)
Used to be a Marshall Fields department store but now maybe a Macy’. Huge like NYC. Kids loved it.
@Peter Thanks for the recommendations!
The city surprised everyone including all of us fellow locals in August this year without much of a notice that they were doing construction around the Bean so they put up a construction fence around it. That’s expected to last until Spring 2024. There’s a lot of events starting up Nov 17 for the holidays with the market, Christmas tree lighting, ice skating at Maggie Daley Park, Lincoln Park zoo lights, etc.
@Kor Thanks for the recommendations! My son is gaga about the Bean and he will be so disappointed.
Do not take an Uber when you arrive…you will sit in traffic forever as the Kennedy is under construction…take the Blue Line to the Clark and Lake stop and then a short Uber or walk to the hotel.
@Joel Thank you for saying this! When I was in Chicago last time the traffic was HORRIBLE.
I would see what the weather is for day 3. If its cold and windy do Shedd, if it is nicer do something outside. Navy pier is kinda Meh, I would not make a special trip down there if you are not there for a boat cruise. The Christmas market is nice at night, if it is a weekend get in line and the line moves fast even if it is wrapped around the block. Athena was good the one time we tried it. We usually try The Village Italian when we visit, Ed Debevic’s & Gino’s East for deep dish pizza.
Enjoyed doing all That in Chicago as well. Just prefer more warmer temps… Enjoy!
@fit2ravels My kids are hoping it’s cold and snowy!
@Jennifer Thanks for your recommendations!
You may find some useful suggestions at https://travel-on-points.com/chicago-travel-guide/
@Maxwell Thanks, I’ll check it out!
The Bean was under construction when we were there in September and cordoned off. Depending on ages of kids the Architectural Boat tours are great. Lincoln Park zoo is great for any age but especially with smaller kids. Just walking along the lakefront is wonderful – depending on temperature and WIND!! Agree with checking out the deep dish pizza for kids!
@Jane Thanks for the info! My son has been talking about seeing the Bean for years now…I may have to break the news to him before our trip.
Bring a jacket and warm clothing it already snowed on Halloween! Get some deep dish pizza. There is a Giordano’s on Jackson right by the Sears Tower if you have time or check out Gino’s another day. The Christkindlmarket opens Nov 17 if you are here it is a nice place.
@Boonie Thanks for the recommendations! I think all three of us need to get heavier jackets. We rarely have a use for heavy jackets where we live.