Chicago is one of our favorite ‘weekend cities.’  For several years running, we’ve visited in the late fall for a night or two.  We have a few traditions we try to keep up when we’re there, but mostly just enjoy the sights and architecture, and relax away from home.

This year was our first time going as a family of three.  As would be expected, the experience was different than prior visits, but we had a blast!

It started with a great deal on our flights, just $71 per person from LAX-ORD round trip.  For more on the flight deal, check out CT’s companion blog post at Cruising Altitude.  We didn’t upgrade our seats, but on account of our status with American Airlines, we booked complimentary ‘main cabin extra’ seats in the bulkhead row.

Since the flights weren’t booked full in main cabin, we used the ‘infant block’ trick- two adults on the same reservation and one lap child, and ended up with the row to ourselves, which was very comfortable and convenient.  Baby Flyer has just started to crawl and cruise, so it was nice to be able to let her roam around a bit in the row without disturbing other passengers.

Even with her new found mobility, she was a good travel citizen, and we kept her well occupied when she was awake.

We decided to rent a car for the weekend.  We like National on account of our Executive membership, that allows us to pick from a range of upgraded cars.  This weekend we chose a nice Buick Enclave, which was great to haul around the baby gear.  In addition, the car seat installed easily, and it was comfortable to drive.

After looking around at the options, we booked two nights at The Palmer House, which is a Hilton property.  It’s located right downtown in the loop, just a block or so from Millennium Park, which is one of our traditional destinations.

This hotel, as we learned, is the longest continually running hotel in the US.  It is also, incidentally, the birthplace of…. the brownie.  You learn something new every day. The property itself is impressive.  It is 24 floors, and occupies nearly an entire block.  The main lobby has a beautiful soaring atrium, with ornate columns, and an intricately painted ceiling.

What made our stay truly memorable, though, were the people at the hotel.  It started with a check in agent who, when she realized that our reservations for adjoining rooms (one for us, and one for CR’s parents who had met us for the weekend) had been mixed up, and the rooms were on different floors entirely, went out of her way to accommodate us.  Way out of her way.  Long story short, we ended up spending the weekend in the expansive and luxurious penthouse suite.  It’s easily the nicest hotel room (if you can even call it that) that I’ve stayed in.  The accommodation included three bedrooms, four bathrooms, and expansive living areas that were easily double the size of our house!

Even without this windfall, I’d recommend this hotel if you’re looking to stay in a central location.  It has a distinctly historic feel, and the service is above and beyond.  We had complimentary breakfast due to my Hilton status in the executive lounge on the 23rd floor.  Each morning, we were welcomed by our server Ernest, who kept things running smoothly and offered great service, and a few laughs.  Baby Flyer especially enjoyed ‘talking’ with him.

The central location of this hotel puts you a block away from Millennium Park, which has one of the nicest, most expansive and creative playgrounds we’ve visited.  The Maggie Daley park consists of numerous themed play spaces, with activities appropriate for kids of all ages.    We were really impressed by the level of imagination and attention to detail in the design, and spent time there both days.  Baby Flyer especially liked the swings, and climbing around the wooden boats in ‘The Harbor.’

We have three main traditions when we come to Chicago.  The first is to take pictures at ‘The Bean’ in Millennium Park (Pictured at the top of this post).  We have them from each trip, including some taken last year when we were expecting Baby Flyer.

The second is to go to ‘The Green Zebra‘ in West Town.  The Green Zebra is an upscale vegetarian tapas restaurant that we’ve always had good meals at.  We stumbled on it our first visit, and now make it a point to go back when we’re in town. The service this time was especially friendly and personal, and we all had a great time, especially Baby Flyer, who always enjoys a good window seat.

Our third stop is to spend some time in the Oak Park neighborhood.  In the past we’ve done the Frank Lloyd Wright tours, but the last few trips we’ve just stopped by Lake Street to grab lunch and do a little shopping.  Especially in the Fall, this area is charming.  As an added bonus, it’s also half way back to the airport, so heading out here early on the day we flew out let us miss the traffic.

Overall, Chicago is a great family getaway.  You can see and do plenty without having to go far from downtown, and if you don’t rent a car, many attractions are walkable.  We look forward to getting back to Chicago in the future as a family and exploring even more of the city!

Travel Well,

-CT

This post is part of Budget Traveler’s Sandbox’s #TravelPhotoThursday, #CityTripping at Wandermum, #WeekendTravelInspiration, and #FlyAwayFriday at Time Travel Blonde. Check out these linkups!