Just back from a long weekend in Chicago. Four days/three nights, and we felt like we made the most of it.
Arrived on a non-stop flight from DC at 7:30 am, and took the train downtown. Couldn’t have been easier, but I suppose if we were heavy packers the train and the 8 block walk from the L stop to the hotel might have been a bit daunting. Checked in at the Hyatt Regency on E. Wacker (great rate and we even got a lake view room!), dropped the bags, and prepared to start exploring. The weather was perfect, but we knew that there is always a good chance that can change at any minute, so we wanted to take advantage of the clear skies for as long as possible.
We had the concierge make us a reservation for the architecture boat tour for noon (the earlier ones were already booked up), so that gave us time to wander around downtown and the Near North area, exploring on our own. I’ve only been to Chicago for quick business trips in the past, so I had never had the chance to really appreciate how beautiful the city is. Stunning architecture, which they are justifiably proud of, everywhere you look. I think the only other city that I can remember where the architecture is such a primal force in the city might be Barcelona, and I notice many of the same Art Nouveau/ Beaux Arts touches everywhere, mingled with beautiful Art Deco and more modern elements. On a bright sunny day, walking along the river (or seeing the river and downtown from a tour boat) is absolutely delightful.
Day 1 (Thursday) – arrive early morning, train to hotel, wander around downtown before heading over to the architecture boat tour – 90 minutes on the water with a good history of the architectural rebuilding of Chicago, and a play-by-play conducted by the Architecture Society of Chicago that gave a detailed description of the building and rebuilding of the city with the architects in the role of great artists. The reconstruction of the city after the great fire led to what may be the greatest concentration of design creativity anywhere, and everywhere you look you see something else that is captivating. Make sure to visit the WGN tower, where pieces of great buildings and great locations from around the world are embedded in the base of the building (everything from the Holy Door of St. Peter’s to the Great Wall of China to the Parthenon to The Alamo to the Berlin Wall).
After the tour we are ready for a late lunch, and head for the Weber Grill (the only restaurant that has been on DH’s list for this trip!) for some charcoal-grilled goodness. It’s worth it just to see the row of giant kettle grills in the kitchen cooking everything on the menu!
That afternoon we booked a hop-on hop-off tour bus. Most of the time I stay away from these things, but when you don’t know anything about a city it can provide a good overview tour, and here it was helpful (although not entirely necessary). It was nice to ride the whole loop for a good once-over, though, and their 3-day pass (the only option) is pretty reasonable. At 4:30 our room is finally ready, so a quick shower and a short nap (we’ve been up since 4 am!) and we are ready to wander out on the town by about 6:30. Hubby has planned to take me to the top of the Wit for cocktails, but when we get there we found out that a swimsuit fashion show has taken over most of the outdoor deck. The place is really too crowded and noisy to have the relaxing drink we were planning on, so after a quick once-around we left (still, we got to ride up the elevator with a couple of supermodels!). We walked up to Frontera Grill (the only restaurant on MY list for the trip) for dinner. The place is packed, of course, but we manage to find seats at the bar for cocktails and ceviche (incredible!) and ended up waiting less than an hour for a table (instead of the 90 minute wait that was estimated). Definitely worth the wait! Duck with apricot mole for me, grilled pork loin with anchos for hubby. Yum and double yum. Nice walk back through downtown to the hotel and in bed by midnight.
Day 2 – Friday
The weather forecast is for a partly cloudy, hot day with a 10% chance of scattered showers. Judging from the extended forecast for the next few days, this might be the best day for outdoor activities, so we decide to spend the day at the beach and a ball game. I’ve never been swimming in the Great Lakes before, so now I have something else that I can check off the list (Ummm, sorry guys, but it isn't the same as the ocean... but I did love the fact that lake water doesn't leave you sticky and salty or the rest of the day!). Since Oak Street Beach is right downtown (across from the Drake, at the end of the Magnificent Mile) it is easy to get to and makes for an easy hour in the cool water and then drying off and grabbing munchies and drinks at the beachside Taco Shack. The timing is perfect to throw some shorts and a cotton t-shirt on over the swimsuit and grab a cab to Wrigley Field, where we picked up cheap tickets in front of the stadium and made it inside just before the game was SUPPOSED to start, just in time to find them pulling the tarp over the field in anticipation of a rain delay. Sure enough, the rain started about 3 minutes later… light at first, then heavy, then almost blinding. Good thing we were still wearing swimsuits! Everyone eventually was forced out of the stands by security because of the lightning in the area, so the covered tunnels and walkways were filled to capacity, but it gave us a chance to enjoy the justifiably famous Chicago hot dogs, and we managed to find a spot on one of the ramps overlooking the crowds as we all watched the monsoon blow through. Three and a half hours after it was supposed to, the game finally started. Cubs eventually won, everyone was happy (and still wet), and we joined the bedraggled throngs and made our way on the train back to downtown. After changing into real clothes, we went outside to find that the rain had completely passed through and it was a beautiful evening. We grabbed a light and very forgettable dinner nearby (sorry to whoever recommended Sweetwater – it was awful) and then walked through Millennium Park (with obligatory pictures at the Bean and the water sculpture), then worked our way over to the outdoor theater where the symphony was doing a Broadway Night concert under the stars. Fabulous way to spend a summer evening!
Day 3 – Saturday
Morning walk up the Magnificent Mile, finishing up a little window shopping just as the Signature Bar at the Hancock Center is opening. We had already been advised to do the Signature Bar (96th floor, I think?) instead of the tower tour, and they were absolutely right. Great views, without the $14 entry fee.
Caught the hop on bus around to Millennium Park for a daytime walk through the park and gardens, and now it is clear that more rain is on the way. The darkening clouds tell us that it is the perfect time to visit the Art Institute museum for a couple of hours. A nice Picasso collection, an excellent Impressionist collection, and the Miniature collection is just plain strange - but strangely intriguing. We live in DC and are really spoiled with having the Smithsonian in our backyard, so it is hard to make myself visit an art museum in any other US city (except NYC). Still, it was a very nice respite from the rain.
Rain over, we grab the hop on hop off for a final tour up Lakeshore drive, past the Navy Pier (which I really don’t get…) and eventually take a nice stroll on the River Walk to Cyrano’s for happy hour drinks and snacks on the banks of the river. Back to the hotel to change for dinner, and we are eventually ready for a stroll up Michigan Avenue, where we popped into the InterContinental to take a look at their famous pool, built on the 12th floor under the dome. DH is an architectural engineer, and he was intrigued by the pool after hearing about it on one of the tours. It is gorgeous and amazing – as is the rest of the hotel. We found out that anyone is welcome to tour the historic part of the building – the concierge has mini-iPods loaded with a self-guided tour narrative that they loan out. The original hotel was built in the 1920s as the Shriner Athletic Club, and the detailing in the interior spaces is magnificent. The whole tour only takes about 30 minutes, and is very cool. Highly recommended to anyone who is interested in architectural detail, the Masons, or the Da Vinci Code (g). We only had time to visit the pool on the first visit, but we came back the next morning to do the entire tour. I’m definitely putting the InterContinental on the short list of places to stay for the next visit.
For dinner, we made reservations at Quartino’s on State Street. Very busy tonight (definitely glad we had reservations), and very fun. Any place that cures their own meats and makes a point of listing where their olives are from on their menu has got to be good. After several courses and much wine, we are ready to walk back to the hotel, and manage to time it to reach the front of the hotel just as the fireworks are starting at the Navy Pier. A very nice light show!
Day 4 - Sunday
Check out, stroll up Michigan Avenue to do the full tour of the InterContinental, then over to Weber Grill for a final lunch before grabbing bags and taking the L back to the airport.
All in all, a very fun weekend. I’m incredibly impressed by the beauty of the architecture and the walkability and ped-friendliness of the downtown area. Although I have no desire to visit in the winter, it makes for a great city break in spring or summer, and we will probably return.
Recent ActivityView all United States activity »
- 1 Planning a 12-13 Day Cali Trip SF to SD
- 2 Train from east cost to west coast
- 3 Walking at Ka'anapali Beach
- 4 Solo Trip to Mid-West
- 5 Luau Worth the Money or Not?
- 6 Arches or Zion?
- 7 Route 66
- 8 3wks in USA, flying in & out of LA, in Jan 2018
- 9 good restaurant near Nawiliwili port, Kauai
- 10 Which National Park summer 2018 with kids
- 11 Charleston Itinerary Feedback Please
- 12 Grand Canyon, Lake Powell, Zion..
- 13 Hiking from Aspen to Crested Butte
- 14 Any nice condo's to stay in Seaside, Florida?
- 15 Uber from Baton Rouge to N.O. Airport
- 16 Where to go for a long winter vacation in Florida, Panama City Beach??
- 17 Driving through Chicago area to Wisconsin
- 18 Restaurant recommendations in falmouth/mashpee, ma area
- 19 Travel Friday Harbor to Olympic Peninsula?
- 20 Trip Report Part 2 (w/teens) - Zion, Bryce and Park City
- 21 Northern California Gardens.
- 22 NEW ORLEANS AND CAJUN COUNTRY...A WEEK-LONG FOOD QUEST
- 23 Adventure Travel in Kenai Peninsula
- 24 Trip Report Part 1 - Carmel/Monterey, Yosemite and Sequoia (w/teens)
- 25 First Time to Seattle-Portland-Willamette Valley
Just back from a long weekend in Chicago. Four days/three nights, and we felt like we made the most of it.