Weekend Trip to Chicago with Husband
 

I am surprising my husband with a belated anniversary trip to Chicago Sept 5 - 7. I have never been, and he has only been once on a business trip. We are 36 and 46, and love to travel. Shopping, eating, and drinking good wine are at the top of the list. We are both active, and enjoy seeing the sights on foot. Here is what I have planned for the trip:


Friday -
- Noon - arrive at O'Hare from Houston
- Take El to hotel (the Peninsula - big splurge for us) in North Loop
- Check into hotel. Late lunch - maybe Giordano's pizza (right across the street from hotel).
- Walk south on Michigan to the Loop, window shopping as we go.
- 3:30pm - Architecture River Cruise
- walking tour of downtown Chicago
- Drinks at Signature Lounge
- Dinner (Blackbird is where I'm currently leaning).


Saturday
- morning run along Lake Michigan
- shopping on Magnificent Mile and Oak Street
- Lunch at Cafe Spiaggia
- 1:30pm - Neighborhoods bike tour - Bobby's bike tour?
- Dinner - either Schwa (if I can get reservations) or North Pond
- Second City E.T.C. show?


Sunday
- morning run along Lake Michigan
- El to Art Institute. Spend morning at Art Institute
- Lunch at Art Institute Cafe?
- Walk through Grant Park and see Buckingham Fountain
- Maybe more shopping
- 5:25pm - Flight back to Houston


I have a few questions about my itinerary -
- How long will it take to eat lunch at Giordano's? I hear that it can be really busy - is that true even for a late lunch?
- Is the architectural boat tour and a walking tour of downtown too much to do in one afternoon? I found Cheribob's walking tour on this site, as well as one in the DK Eyewitness book. The DK Eyewitness book says it's a 3 hour walk, but it looks like it's just 1 mile. Should I save the walk for Sunday morning? Or will it be better during the week, when the buildings are open, people are working, etc.?
- Has anyone done the Bike tour? The Saturday afternoon tour goes through many neighborhoods we won't be seeing, so it looks fun. But, it may be too much to cram into the weekend? Any thoughts?
- I'm not sure about a nice dinner and then Second City on Saturday night. I think we'd have to go to the late show (11pm) if we did that. Is Second City worth it? Or would it be better to just have a great dinner, and then be more well rested for Sunday?
- Any other suggestions for lunch on Sunday? I read the Art Institute Cafe was nice, but I'm open to other ideas.

Any other comments on the itinerary would be appreciated. So far, I've only booked the flight and the hotel. I really want this to be a fun trip, and to pack as much as I can into it (without wearing us both out!). Thanks very much.

Flights into ORD are often delayed. Also take into account getting off the plane, getting your bags, walking through the airport, finding the train, waiting for the train, etc. I'm not sure you'll have time for Giordano's and then the 3.30 Architecture Cruise, especially if you take the train into town. I would consider a later reservation for the cruise, or going on another day.

I've never been to Giordano's for a late lunch, but the deep dish pizzas take a while to cook. Went there for dinner one night and was told to expect 45 minutes for the pizza to hit our table.

friends who were there recently raved about a seqway (sorry @ spelling-the motorized schooter like thing you stand on and ride)tour of chicago. Might be something fun to do instead of bicyle tour.

Highly, highly recommend the Segway tour. (We do these everywhere we go that they're offered now.) My husband never wants to turn his in at the end. The route is incredibly scenic and riding the Segways is great fun.

For a walking tour, I highly recommend Terry Sullivan

[email protected]

He's a private guide, but his rate was very reasonable. Advantage - you go whenever you want and wherever you want - and he has excellent recommendations.

I think the best way to see/enjoy the neighborhoods is the double decker buses. The views (and photo ops) from seats on the open air upper deck are magnificent. You can see SO much better than by walking around.

I can't give a time estimate on lunch at Giordano's either, but the location on Superior/Rush is probably the busiest. You may be seated faster at their other location on Lake & Michigan (behind Prudential Plaza) which tends to have less people. They also have a restaurant at Randolph & Franklin in the west loop.

To reach the Art Institute, don't take the L. It's easier to catch the Number 145, 147 or 151 bus southbound at the corner of Superior & Michigan, about 10 steps from the door of the Peninsula. They will drop you across from the door of the Art Institute at Adams.

Also, on the Wednesday or Thursday before you leave, check the CTA site (www.transitchicago.com) to see if there will be any service interruptions or detours on the Red or Blue Lines that weekend.

You didn't mention it, but 3-day passes would probably be a good idea. They're $12 each and allow unlimited rides on all CTA trains and buses. Passes are available from the vending machine at the ORD station.

I recently read another post where the people did multiple architecture tours during their trip. They bought a family membership to the Chicago Architecture Society. It gave them a discount on the river tour and many free walking tours. It sounded like a fun idea.

We were in the loop on Sunday and did a Segway tour. It was a great way to see lots of the lakefront in a short time. And it was fun.

Wow - great minds think alike. I'd left CStoneTx's note open and replied before I read all the other posts about the Segway tour.

Just a note about Giordano's - I went for a late lunch on my first trip to Chicago (I think to the Randolph location, though). I think we got there around 1:30 or 2:00. We were seated immediately, but it does take the pizzas a long time to cook. We ordered appetizers to tide us over, which came out pretty quickly. I actually preferred Lou Malnati's to Giordano's, but a) location seems like a big factor for that particular meal, and b) you will find all kinds of threads debating who has the best pizza in Chicago!

We took a 4:30 CAF river tour and it was perfect - tour, nap, dinner, Second City, in that order!

Second City is not only a Chicago institution, but it's also a blast. I'd highly recommend the Adobo Grill for dinner, and then see the show. Make sure you have reservations, as it is quite busy. It's not very upscale, but it's great for a pre-show dinner. Also, the guacamole is fantastic.

Have fun - this sounds like a fun trip!

These are some great ideas and suggestions. I will definitely look into a Segway tour.

I was planning to get a pass for the metro/subway/buses, but didn't know which one to get. The three day pass sounds perfect.

Thanks for the feedback on pizza lunch on Friday. It sounds like Giordano's may be a bit of a stretch time wise. Perhaps it would be better to go there on Sunday for lunch. (Or another pizza place - I have read all the posts on the great pizza debate, and have no strong preference for any of them, since I've never been to them - except Uno's when it was in Houston, which I really liked, but which I hear is different than the original in Chicago) Maybe the one by the Prudential Plaza - that one is right by the Art Institute. Any other pizza places near there? Gino's and Lou Malnati's seem to be a bit out of the way from where we'll be.

That being said, any suggestions for lunch on Friday? Since we won't have eaten since breakfast, we'll be hungry, and will want to eat pretty close to the hotel, I would imagine. What about Quartino's? I've read good things about it, and it looks close on the map.

Thanks again for everyone's advice!

CStoneTX, the best pizza places in the city aren't near the Loop, Mag. Mile or River North areas but further away in the neighborhoods on the north side. Which one just depends on if you are looking for thin-crust, deep-dish or stuffed. If you still have your heart set on Chicago-style deep-dish pizza, the ones usually mentioned are OK, though.

Here are my suggestions:

On Friday, go to Fox & Obel on E. Illinois (in North Pier, a couple blocks west of Navy Pier), which is an upscale gourmet market. They have a very nice cafe which overlooks the Chicago River where you can get a late lunch. You won't be too terribly far away from your original intinerary route for going to the Architecture River Cruise (and I trust that you are taking the Chicago Architecture Foundation's cruise, by the way).

After you are finished with the cruise, you should really visit Millennium Park first. Only three blocks south on Michigan Avenue from the River. There is a free downloadable tour of Millennium Park which can be gotten from their website, if you wish.

I always recommend this book for those visiting Chicago (or even those living here): Gerard R. Wolfe's "Chicago: In and Around the Loop: Walking Tours of Architecture and History". In the event you don't wish to buy a walking guide book, if you go to the Chicago Loop Alliance's website, you will find three free downloadable - to your computer or an MP3 device - walking tours of the Loop (theatres, art and landmarks).

Blackbird is a fine place. Don't know the type of ambiance you are desiring, though, especially since this is your anniversary.

On Sunday, the Art Institute opens at 10 a.m. Do you want breakfast beforehand? If so, recommend Yolk on S. Michigan Avenue. NOTE: It's very popular, so the later you go, the longer the wait for a table. A couple of weeks ago, I took my brother's girlfriend, visiting from out of town. We got there by 8ish and there was about a 15 to 20-minute wait even then. But the Garden Cafe in the Art Institute is a nice place, too.

About your question on when to take the walk. You are asking about going into buildings...to which ones are you referring? You know that 9/11 changed many things in our lives, casual entry into structures being one of them.

By the way, I'm very happy to see you are thinking about going to Schwa. Too many visitors come to Chicago and never get outside of the Loop, Mag. Mile and River North areas - which means they are missing the BIG picture. Glad you aren't making that mistake.

<i>On Friday, go to Fox &amp; Obel on E. Illinois </i>

This is the best grocery store/market I've ever been in.