If you are planning to go to an observation deck like the Willis Tower (formerly known as the Sears Tower) or the John Hancock Building, an elevator pass is ~$20. The BEST tip is to actually go up to the lounge in the Signature Room Restaurant. It's on the 95th floor of the Hancock Building so only a couple of floors different than the observation deck. So you can buy a drink and sit right by the glass. Elevator is free so the money buys you a couple of drinks. Much better atmosphere as well.
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Also, if you are staying downtown, take the BLUE train instead of a cab. It is so much faster and also much much cheaper. You'll be going down the tracks towards downtown past all of the cars sitting in a traffic jam (which seems to be 16hrs each day). Take the train downtown then hail a cab to your hotel.
Just watch out for inattentive train operators...a few months ago, he/she failed to apply the brakes and ended up in the escalator...youtube it if you are interested.
Love Chicago, so let me put my two cents.
If you're arriving at O'Hare, especially during rush hour, take the Blue Line train in to the Clark/Lake stop. You can either walk to your hotel or catch a cab from there.
You can take the train from Midway, too. The Orange Line.
The Art Institute of Chicago is amazing, as are other museums people suggested.
My favourite Pizza is Lou Malnati's. The others listed, Giordano's, Uno and Due and Gino's East are also excellent for deep dish.
As for dining, The Purple Pig is really good. I'd also suggest the Weber Grill, Ditka's, Eatlay is kinda cool (like a big cafeteria), Heaven on Seven (cajun-creole). It's Chicago, you can't swing a cat without finding a good place to eat, and when in doubt, check out ratings on Tripadvisor.
Another recommendation, Blommer Chocolate. Their factory is close to downtown and the smell when you get close to it is intoxicating.
For entertainment, Buddy Guy's and House of Blues are cool, but also so is Blue Chicago downtown, and on the north side, B.L.U.E.S. and Kingston Mines - smaller places but great music and cheaper drinks than the name clubs.
Have a blast.
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The Green Mill used to be owned by Al Capone and is a cocktail bar with good atmosphere. Went there on a Tuesday, good jazz band and the kind of place where talking during the music is minimal. A throwback
Buddy Guy's Legends has had good blues when I have been there and word has it Buddy often shows up when he is not on tour
So I was actually in Chicago this week on business, and got to validate my last point. Buddy showed up, and the man sat down at the bar next to me (!)
I chatted with him a while, told him he was looking great. He said "well, son, I think you might need glasses".
He joined the band to sing a couple of songs. Awesome. So the club is going to be good either way, but if he isn't touring, then definitely worth the visit!
* In fact, the reason I found this out is that I had gone to a bar to watch the Flames instead of going there one night. That game was the infamous Getzlaf hand over the line game. Meanwhile, at Legends, Eddie Shaw (Muddy Waters old sax player) was playing, his guitarist didn't show, and Buddy sat in all night. I found out the next day when I went there for lunch before heading out.
Also, when I was there, all hotels downtown were booked, not sure what was going on. I stayed in Evanston, a nice university town 20 min north of downtown. If you find yourself there, Found is a very good restaurant. One of those farm to table places.
If you are situated in Chicago I may not venture there, but it was a pleasant surprise
Truly an arts hotel, The James features two gallery spaces with rotating exhibitions showing current projects by Chicago-based and international artists. In addition, The James is a mere block away from the Magnificent Mile, where visitors can explore Chicago’s vibrant museums and visit the city’s many excellent restaurants and eateries.
Rick’s side by side award-winning restaurants are in Chicago. The casual Frontera Grill was founded in 1987 and received the James Beard Foundation’s highest award, Outstanding Restaurant, in 2007. The 4-star Toplobampo, which served its first meals in 1991, earned the Beard Foundation’s award for Outstanding Restaurant in 2017 — a unprecedented feat for side-by-side restaurants. The wildly popular, LEED GOLD-certified, fast-casual Xoco has been around since 2009, serving wood-oven tortas, steaming caldos, golden churros and bean-to-cup Mexican hot chocolate. Rick’s quick-service Tortas Frontera have changed the face of food service at O’Hare International Airport, while Frontera Fresco has brought Frontera flavors to several Macy’s stores and Northwestern University. His award-winning Frontera line of salsas, cooking sauces and organic chips can be found coast to coast.
In 2016, he opened two new restaurants in Chicago’s bustling West Loop neighborhood — the Baja-inspired, wood-fired Leña Brava and the adjacent Cervecería Cruz Blanca, a craft brewery and Oaxacan-style taquería. Both have earned critical acclaim. Also in 2016, he opened Frontera Cocina in Disney Springs.
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I highly recommend the Wicker Park Inn. It's basically a bunch of walk-ups in the hipster neighbourhood of Chicago. Nice rooms, and very convenient to restaurants, the L-line, etc.
What we have tentatively planned so far (again, we need to entertain two young children):
- Millennium Park
- Maggie Daley Park
- Oak Street Beach
- Navy Pier
- Chinatown
- Jays vs Sox at Guaranteed Rate Field
- The 606
And of course, there is Chicago food:
- Pequod's Pizza
- Garrett Popcorn
- Al's Beef
- The Kalamata Chicken at The Athenian Room (watch the Letterman interview with Tina Fey on Netflix if you don't know what I'm talking about)
- Dim sum at Cai
Are you thinking about stopping in Milwaukee at all during your trip between Minneapolis and Chicago?
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If you like dive bars, The billy goat tavern was fun. A lot of the second city guys used to go there back in the day. Neat little bit of history around it. Plus it is near the Tribune building with is interesting with all the pieces from around the world embedded in the building.
The old Lounge Ax club is now Millie's Supper Club. The Lounge Ax was featured in this scene in High Fidelity.
I saw a show at the Lounge Ax in August 1997. Number One Cup was the feature band (I love Pavement rip-off bands) with Verbena opening. During the middle of Verbena's set, Scott Bondy left the stage and then came back a few minutes later and announced that Princess Diana was in a car wreck and that she had died. I was horrified but assumed it was a joke because Bondy seemed drunk during the performance. This was before cell phones (or even the internet) were ubiquitous so most people were kinda in shock, not knowing if what Bondy said was true. When my buddy and I got back to our hotel room, we found out it was true. So I have some really vivid memories of that night at the Lounge Ax.
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+1 for Buddy Guy Legends bar. Not really a blues guy but loved it. Been a couple times.
-1 for any Chicago style pizza, my opinion only.
United Center was a tomb when I went, but Flames won so I was happy.
Theatre district is great, if that's your thing.
Otherwise, great suggestions for things to do.
We don't get downtown enough to know any good restaurants. There must be great ones... there is nothing in NW burbs near us. Other than the Portillo's hotdog chain!
This Independence Day, join us at Navy Pier for the best free Fourth of July fireworks display in Chicago: the Aon Summer Fireworks, presented by Miller Lite!
Navy Pier is the destination for spectacular fireworks in Chicago, perfectly synchronized to music on Lake Michigan. Our biweekly Aon Summer Fireworks shows occur on Wednesdays and Saturdays throughout the summer, from Memorial Day through Labor Day. Be sure to check the schedule for additional shows added throughout the year.
Whether you’re viewing them from the dock or aboard an evening cruise, fireworks are the perfect way to end your day at Navy Pier!
Most get their views of Chicago from the sidewalk, the back of a cab or maybe an El train, but the best way to see the city is from a boat. Hop on board a tour and you'll be treated to amazing views of beautiful buildings, fireworks and the Chicago skyline. You can cruise down the Chicago River learning about the city's history or eat dinner while gliding across Lake Michigan. Trust us: most of Chicago's best attractions look even more gorgeous from the water.
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