1. Trump Hotel Chicago for All-Out Kid Luxury and Amenities
If style and posh accommodations are top of mind, we think Trump Hotel Chicago is the way to go, no matter what your age may be. The hotel has an amazing riverside location right in the Loop with views from the 16th floor Terrace (the best spot to catch Navy Pier fireworks). And now with a new Wendella boat stop added just outside the doors at the Riverwalk, families can jump onboard for an historic architectural river tour (seriously, there’s no better way to see the city in the summer).
If we were tweens, we’d love the free WiFi, Wii or Playstation rentals, and special spa treatments, but there’s also a pretty pool, board games, and cookies at turn down. Point being, kids won’t be lacking for any entertainment, though you’ll need a stretchable wallet to partake in everything Trump Chicago offers. Room rates in mid-May start around $445 a night.
2. Doubletree By Hilton Hotel Chicago for the Outdoor Pool
Notorious Chicago winters mean you’ll rarely see outdoor pools at Chicago hotels, but DoubleTree is one of the lucky few to boast a sweet summertime pool (as well as an indoor pool). And that outdoor rooftop pool signifies a respite and retreat for families navigating the busy, bustling city. Break up walkable visits to the nearby Mag Mile and top attractions like The Art Institute of Chicago and Navy Pier with a dip in the pool for the kids and some chill-out, chaise-lounge time for mom and dad. Make sure you snag some signature chocolate chip cookies at check-in, too. Room rates start at around $249 a night.
3. Hotel Lincoln for Local Style, Beaches and the Zoo
Opened just last week, this kitchy-cool Lincoln Park hotel sits just a five-minute drive north of the city and offers a tremendous gateway to Chicago’s North Side. We can't say enough about the location, the Perennial Virant restaurant, and all the local color inside, but families in particular will totally dig the immediate access to Lincoln Park -- Chicago’s largest park at 1,200 acres and home to the free Lincoln Park Zoo, Peggy Notebaerdt Nature Museum (check out the Butterfly Haven), Chicago History Museum, bike and running paths, tennis courts —the list goes on and on.
And we didn’t even mention North Avenue Beach, yet. Great shops and casual eateries surround the hotel (take the kids for fondue at Geja’s). Inside the hotel, playfully cool Family Suites come equipped with two full bathrooms (that’s right, TWO), a main bedroom with a king and an additional sleeping area with two bunk beds. Room rates start at around $186 a night.
Other worthy mentionables we’d easily recommend are:
Affinia Chicago for its roomy, well-laid out rooms and prime Gold Coast location just off Michigan Avenue and steps from American Girl, Water Tower Place and – drum roll – the Lego store.
· The James for a chic Streeterville location and cool kid-rentals like Nintendo Wii, Paul Frank Bikes and Paul Frank PJs.
· Hotel Palomar Chicago for a welcoming spread that includes a welcome gift, recommended kid activity itinerary, kid-friendly “mocktails,” kid-sized robes to follow the pool, and a comment card for kids to share feedback.
Got a different suggestion for tweens in the Windy City? Tell us in comments below!