Illinois (Chicago)

Chicago is a city that rivals Boston in my heart which says a lot since Boston is my hometown. I’ve been here a few times but my I highly recommend the summer for a visit, or at least during baseball season.

History, museums, parks, shopping, “The El”, theatre, every possible foodie option, sports and festivals. Chicago has it all – something for everyone.

Most of the overview below is from a trip I took in July 2017.

A Chicago Dog – Wrigley Field

Getting There/Where To Stay

The main airport is O’Hare, but check options into Midway as well. No rental car needed – take a cab to your hotel and then use your feet to get around this large but walkable city.

As with any major city, there are tons of accommodation options. Location, location, location. I used some credit card points and splurged on a club level room at The Langham. Did this for two reasons – the spa, the best I’ve ever been to in the U.S. and access to The Langham Club, a private haven for guests with club rooms.

The Langham club is a 4000 sq ft lounge on the top floor of the hotel with panoramic city views, daily breakfast buffet, all-day refreshments, afternoon tea, cocktail hour with hors d’oeuvres, reading library and business center – all included with your room. The service and food were amazing, one of my best hotel memories ever. It was so nice to have access to extensive breakfast options without leaving the hotel, and a nice way to save a little money by taking advantage of pre-dinner cocktails here instead of in expensive restaurants. Access also provides butler service, complimentary garment pressing service and daily access to the fitness club. Spoil yourself!

The Langham, Chicago

Chuan Spa

Just writing about this makes me want to jump on a plane. I often daydream about returning to the Langham and just staying in the hotel for spa treatments all weekend.

The Chuan Spa is an oasis offering Chinese-based spa services. The treatment rooms themselves were gorgeous. There is an indoor heated pool on the same level as the spa for lounging between treatments.

Reading the spa menu is like taking a trip to the Orient. So many unique offerings to choose from. My best memory of my spa day was the mud wrap. My treatment took place in a huge room. It involved multiple steps, but once the mud was applied I was wrapped in a huge piece of foil (for lack of a better description) and enjoyed a head massage while absorbing the benefits. It was heavenly. They offer Chinese medicine consultations, but schedule in advance to ensure the appropriate staff are available. Check out moxibustion.

Things To Do

Magnificent Mile

Shop, shop, shop. Make sure you have comfortable walking shoes – it is a deceivingly long mile. I found a little strip of gorgeous boutiques onEast Lakeshore Dr/Oak St, a left turn off Michigan Ave on the northernmost side, for those looking for something a little special other than the deals at the retail giants.

The Loop

The Loop represents the lively and ecclectic neighborhood area of Chicago where you’ll find the Willis Tower (formerly the Sears Tower), Chicago’s largest skyscraper with the famous viewing deck on the 108th floor.

Also in The Loop (southern end of Michigan Ave) is Grant Park/Millenium Park. Take a stroll – there was a lot to see here including the famous Cloud Gate sculpture, the famous Buckingham Fountain and the Chicago Institute of Art.

TIP: If you visit in summer, look up the dates for Taste of Chicago. It takes place in Grant Park. I caught this on my first trip to Chicago and it was a fantastic outdoor eating extravaganza at the foot of the best museums.

Cloud Gate sculpture, Millenium Park
Shedd Aquarium


In addition to the Chicago Art Institute, check out the famous Field Museum (dinosaur lovers paradise) and the Shedd Aquarium. I did the Shedd many years ago and they offered a headset audio tour which was nice.

Field Museum, Chicago

Wrigley Field

It would be a crime not to attend a baseball game during the season. The quintessential baseball experience is available here – ticket or no ticket, you can still mill the crowds, bar hop and get your fill of Chicago Hot Dogs and sausages. A must-do on game day.

Can’t get a ticket for inside the stadium? Check out Wrigley Rooftops. A row of houses facing the stadium have transformed into viewing platforms. Tickets can be purchased for some, others are private.


This city has it all so take advantage. Highlights and lowlights below.

  • Giordano’s – famous deep dish pizza spot. Waited forever for a table and another forever for mediocre pizza. I much prefer Pizzeria Uno.
  • Lou Malnati’s – another deep-dish institution, another long wait, much better pizza than Giordano’s. The wait was so long I walked down the street and discovered Portillo’s, the place hot dog dreams are made of
  • Portillo’s – the Soup Nazi meets hot dog shack, my absolute favorite spot in Chicago, hot dogs, polish sausages, cheese steaks all served up efficiently so get in line
  • Gibsons Bar and Steakhouse – classic steakhouse with the standards – aged steaks, lobster tails and crab legs in butter. Nothing exotic.
  • RPM Steak – this was the hot new table in town so I got a reservation. It promised to be an extremely expensive but impressive meal, however the service was terrible and the waiter started listing all the things they were out of before we even got drinks. So we left. It’s Chicago. Get a hot dog or a pizza.
A perfect Polish sausage at Portillo’s while waiting on a table at Lou Malnati’s
Gibson’s Steakhouse

This is all for now for Illinois. If you’ve done Chicago and want a similar experience, go to Boston! See my Massachusetts page for the details.

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