Two days is plenty of time to do so many things in this vibrant and cosmopolitan city. This trip was just two days, one night for a 15 year wedding anniversary and, despite the wide variety of experiences, did not feel rushed! Inspired by The Bear, we had ambitious eating goals, but the architectural phenomena may have been even more appealing during this Saturday morning to Sunday evening stay in the Windy City.

Places to stay

*Stroll Lake Michigan - just a short walk from the Ambassador*

Looking for a mid-range hotel in a quiet neighborhood, but still very walkable to many local attractions? Try the Ambassador Chicago. It’s not far from the lake, the Magnificent Mile, and two local spots to eat for breakfast and dinner that make it worthwhile to stay in this charming property.

Doing it up big in Chicago? Two places to splurge on luxury are the St. Regis and the Four Seasons. Choose the St. Regis if you are a foodie and love great views and the Four Seasons if the spa is your thing. Can’t go wrong at either place.

The Godfrey Hotel is another good choice, with a rooftop bar, spa, and location near foodie destinations (see below for more on that).

Places to eat

If you stay at the Ambassador, nearby are two neighborhood gems. The 3rd Coast Cafe for breakfast and Mario’s Table for a lovely Italian dinner - we tried Veal Saltimbocca, Chicken Parmesan, and a shared salad with an amazing vinaigrette.

Near the Godfrey, Indienne is outstanding. The restaurant has a vegetarian and pescatarian tasting menu, but we sat at the bar and ordered a la carte - reasonable prices, great food, and excellent service.

Mouthwatering pork belly bbq at Indienne

If you watch The Bear, Eater has a great guide to the 60+ restaurants featured on the show. Two we tried were awesome: Avec and Tortello. Amazing lunch on the way to the airport at Avec - tried their famous chorizo-stuffed dates, had a delicious lamb burger, and shared a salad. Perfect meal. Tortello was great for dinner - the tagliatelle and fennel salad were excellent and we were tempted by the take home cooking kits (if checking luggage instead of carrying on, would have definitely returned home with at least one of these as souvenirs.)

Chorizo-stuffed dates and lamb burger with chips at Avec

If sightseeing near the Loop, try breakfast at the Wildberry Pancakes and Cafe . It’s a very popular place with an enormous line when we went there on a Saturday morning - we almost left to find an alternative but were glad we waited and understood why the place was so popular. The barbacoa chilaquiles with a side of pancakes was enough to split between two people and outstanding. Service here was also friendly and fast.

Things to do

Top of the list and not to be missed is the Chicago Architecture Tour. This experience was amazing. Appropriate for all ages, so informative, great sites and information about the history of so many historic landmarks in Chicago. All in a 90 minute boat tour!

Second on the to do list is the Frank Lloyd Wright Museum and tour. The experience includes a guided tour of the home and studio and a self-guided audio tour of the surrounding neighborhood featuring homes designed by Frank Lloyd Wright. Such an intriguing and educational way to spend an afternoon before heading home from Chicago - we stopped here on the way to the O’Hare airport and the museum conveniently stored our luggage during our tour..

It’s one of the most touristy things to do in Chicago, and relatively expensive if you include both entrance fee and access to the skydeck, but we thoroughly enjoyed seeing panoramic views of Chicago at the Willis Tower (formerly known as the Sears Tower) and there’s a great food hall on the ground floor of the building.

Eat and Tour Addendum

At a follow up visit to Chicago, we tried the Dining Room at Kendall College, a unique eating out experience and a great way to support culinary students. You can experience a $45 three-course tasting menu (with an optional $20 wine pairing) and added to this are a welcome cocktail tasting, bread service, and amuse-bouche. The service is impeccable and there are sweeping views of iconic Chicago locations. The museum just outside the dining room also showcases interesting historical cooking artifacts and we really enjoyed seeing the flyer board featuring opportunities for the students in the community. The dining room is open for dinner during the week with some more limited options for breakfast.