British honeymoon couple
Chicago covers a lot of real estate and is a food destination city so please bear with just a few questions so we can give you useful responses.
When will you be here (month) and what days of the week?
Where in Chicago will you be?
What kinds of foods or cuisines do you like or dislike?
What kind of budget did you have in mind?
Assuming you're going to be staying somewhere near the John Hancock building, which is at 875 North Michigan Avenue (and may be the most recognizable building in the Chicago skyline)...
For your expensive dinner, there are only a few (less than a dozen) truly expensive restaurants in Chicago. These are places where you'll spend over USD250 per person, including moderate alcohol and tax/tip, and some are even higher than that. These are characterized by the finest cuisine, and armies of waitstaff providing the finest service. Most are rather formal (jackets required for gentlemen).
The very best restaurant in the United States is here; it's called Alinea, and it's as amazing for the presentation techniques as it is for the delicious food. It's truly a once-in-a-lifetime experience (unless you are fortunate enough to go more than once!). They currently use a ticketing system for reservations, and it is in VERY high demand, so you would need to find out when they go on sale for your dates, and figure out how to buy them immediately. EDIT - Thanks, kathryn, for posting additional information below about ticket sales!
If you have trouble getting into Alinea, I recommend TRU as the first backup. They serve wonderful contemporary American cuisine, which I think would be a terrific approach for visitors from the UK, and are as outstanding as any restaurant in Chicago other than Alinea right now. It's less than half a mile from the Hancock so you could walk there.
Our other high-end restaurants include Spiaggia (our only high-end Italian, only a few blocks from the Hancock, but you probably have plenty of high-end Italian at home), Everest (contemporary French/Alsatian, in the Loop a mile south of the Hancock, on the 40th floor with a great view looking out over the city), and a few others (Sixteen, L2O, Les Nomades). A few more may open between now and May, including Grace, the new restaurant from Chef Curtis Duffy.
If $250+ is more than you wish to spend, there are plenty of options below that price point. There are several excellent restaurants that are almost at that level, with fine food and fine service but a bit lower in price ($110-140 or so per person) and not as formal (jackets not required). Two serve contemporary American cuisine and are owned/run by chefs who won the prestigious James Beard Award. North Pond is a couple miles north of the Hancock, and is unique because it's in the middle of Lincoln Park - the park itself, not the adjacent neighborhood of the same name. It faces its namesake pond (the renovated building was once a warming shelter for ice skaters on the pond) and the city skyline looms over the opposite shore. It may be the most romantic restaurant in Chicago. Ask for a table in the front room with the full-length windows facing the pond. The second restaurant in this category is Naha, which is in River North, about 3/4 mile from the Hancock. Also thoroughly excellent. A third restaurant serves creative contemporary Mexican cuisine, which I'm guessing you don't find much in the UK. It's called Topolobampo and it too is owned/run by an award-winning chef, Rick Bayless. It's about 3/4 mile from the Hancock. Topolobampo makes reservations available on Opentable.com exactly three months ahead of the date of the reservation, and they fill up VERY fast, so make sure to book when the date you want becomes available.
Those are the places I recommend most for a special occasion dinner. We have many, many more restaurants here, of course. Here are a few of my favorite places that aren't as expensive, probably well under $100 per person. Sable is half a mile from the Hancock and serves contemporary American cuisine in a small plates format. Everything is amazingly delicious. Don't miss the sweet corn creme brulee, a savory riff on the classic dessert. They also have outstanding artisanal cocktails. Another excellent restaurant is GT Fish & Oyster, which specializes in seafood in a small plates format, also has nice craft cocktails. About 3/4 mile from the Hancock. Piccolo Sogno Due is 3/4 mile away, and has excellent Italian cuisine. There are many, many more, but these are three of my favorites, places where I keep going back over and over because the food is so very, very good.
All of the above places except Alinea accept reservations for free on Opentable.com Many of them don't do so six months ahead of time, so you may need to wait a while before being able to make a reservation there. Alinea and Topolobampo are the toughest reservations to obtain, as noted above. When you make your reservations, I would encourage you to let them know you're on your honeymoon! (If you reserve on Opentable, there's an area for comments and special requests where you can mention this.)
One other thing you might try while you're here, maybe for lunch, is our delicious local specialty of deep-dish pizza. It's unlike pizza anywhere else (it's not like the bready thick-crust pizza you find in some other cities). One good place where you can get it a few blocks from the Hancock is Pizano's on State.
For an outstanding breakfast a few blocks from the Hancock, go to the Original Pancake House on East Bellevue. They have excellent omelets and pancake dishes. Their specialty is a gigantic puffed-up cinnamony apple pancake. They also do an excellent German pancake using the same batter, but without the cinnamon and apples.
Oh, and as you make your way down Route 66, St. Louis will be the first big city you hit after leaving Chicago. For a cheap meal there, go to Bogart's Smokehouse, which has outstanding barbecue, an American specialty which varies by region and for which St. Louis is well known. They get very busy, but it's worth waiting for. For an upscale meal in St. Louis, I recommend Tony's or Niche. Both have outstanding food and service; the atmosphere at Tony's is more traditional, at Niche more contemporary.
I notice in your other post that you are interested in going to a baseball game, but you'll miss games while you're in St. Louis because the Cardinals will be out of town. The Chicago Cubs will play here the evenings of April 30 and May 1, and the afternoons of May 2 and May 3. Since you're interested in baseball, I would encourage you to see a Cubs game. Wrigley Field is well known as a classic baseball stadium, one of only two remaining stadiums that were built before World War I. Before the game, try a Chicago-style hot dog at Wrigleyville Dogs. For schedule and ticket information, see www.cubs.com (We have two major league baseball teams here, but the White Sox will be out of town during your stay.)
Feel free to ask more questions, enjoy your honeymoon, and congratulations!
Tickets for Alinea for February and after have not yet gone on sale.
Here is where they will post the on sale dates:
Looks like they are doing it on a Wednesday approx 2 months ahead for each month. BUT they do NOT pre-announce what time that day.
November will become available Wednesday, September 12
December will become available Wednesday, October 10
January will become available Wednesday, November 7
From what I have observed, tickets may take a few hours to sell out, especially since the whole month goes on sale at once. The 2-tops go first, as do the Fri/Sat tables. Tables closer to 8pm will cost more. Since you are going to be here on a Wednesday/Thursday, you won't be fighting with quite as many people for tickets.
Thank you nsxtasy! That info was so helpful, with our tight schedule, we are thinking Topolobampo would be good for the day we arrive, early dinner and hit the Sky Deck for some twilight views!, Then I think we'll try and get a table at North Pond for Thursday night; its sounds very romantic!
Chicgail.. I haven't been logged on over the holidays, but my Partner was completely wrong about our accomodation.. we are staying on North Michigan Avenue. Do you have any other suggestions on top of nsxtasy's?
We'll be heading to the Original Pancake House before we leave for definite!
Thank you for the St Louis Recommendations.. Bogarts seems very popular.. we'll hit there!
>> my Partner was completely wrong about our accomodation.. we are staying on North Michigan Avenue.
Just to orient you...
The stretch of North Michigan Avenue from the Chicago River (roughly 300 North Michigan) to Oak Street (1000 north in our numbering system) is known as the "Magnificent Mile". That stretch, along with nearby side streets, contains luxury shopping and our top luxury hotels.
The mile of Michigan Avenue south of the Chicago River, which includes North Michigan Avenue and, south of Madison Street, South Michigan Avenue, is part of the Loop, Chicago's historical and commercial downtown. To the west are high-rise office buildings, and to the east are Millennium Park, Grant Park, and the Art Institute, our biggest and most well-known art museum. There are hotels along this stretch as well, so it's possible to be on North Michigan Avenue without being on the Mag Mile. But since you previously said you were on the Mag Mile, your partner couldn't have been off by more than a few blocks - a mere technicality! :)
We're finally in Chicago; been a struggle getting our bearings but we're hoping to make it to GT Oyster Bar tonight.
So far we found a place called Giordano's last night, deep dish Pizza, was really good! The original pancake house this morning.... The apple pancake is massive, I have never seen anything like it!
Also had a few odds while seeing the sights; a hot dog stand "Chicago Style Dog", Al's special Italian Beef sandwich, and we treated ourselves to Ghiradelli Ice Cream Sundae!
Keeping a blog online!