High Roller: The Best Local Splurges Worth Your Dough

Use any excuse you like, be it blowing off steam or supporting the economy, but sometimes you just want to splurge. You've come to the right place, because we found a ton of ways to drop a ton of cash in Chicago, and we're not keeping secrets. Got a credit card handy? Whip it out and have some fun. Talk is cheap.
EAT
Dinner for two at Alinea:
Forget casual dating. This is I love you. Dinner for two at Alinea starts at $390 for two people, and don't even think about walking in. Call ahead (very far ahead) for reservations. A mind-bending molecular, gastro-astronomical (yes, we just made that up!) dinner is served each night between Wednesday and Sunday, and you'll want to make a night of it. Last time we looked, we counted 21 courses in this culinary adventure. Go wild. Alinea, 1723 North Halsted Street (at Willow Street); 312-867-0110.
The Large Australian Lobster Tail at Gibson's:
Lobster is perfect. Maybe we're interjecting our own preferences into this one, but come on. It's delicious, it's gorgeous, in sum, it's money. The biggest, most bad-ass lobster you'll find in Chicago is at Gibson's, the quintessential Chicago steakhouse. You'll find white linen, dim light, and a piano. This is how you do it. Gibson's, 1028 North Rush Street (one block South of Maple Street); 312-266-8999.
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WEAR
The Medor Clutch from Hermès
With all the action your credit card is about to see, it deserves a luxurious place to rest. We'd pick the Hermès Medor Clutch, which can be yours for $4,850 if you pop into the new Hermès location in Chicago. Hermès, 25 East Oak Street (at Rush Street); 312-787-8175.
Rent The Bedford Necklace from Adorn:
It doesn't matter what you wear, as long as you decorate it with this baby. The Bedford Necklace is a sapphire and diamond treasure that retails for $45,000. If traveling light is more your thing, why not just rent it for your next high society appearance at a mere $990 per day. Think of it as a way to test-drive your next big purchase. Adorn specializes in jewelry rental for weddings, but we think you should have gorgeous jewels like this one any day you like.
Gary Graham's floral organza dress from Robin Richman:
A spendy roundup would be incomplete without shopping. Robin Richman is our go-to for shopping splurges (and sometimes wishful browsing!). The boutique's got the hook-up for all your luxury fashion needs and wants. We'd pick Gary Graham's floral organza dress. At $1,370, it's a necessary addition to our dress collection. We think it matches the yacht perfectly. (Keep reading).
PLAY
The Privilege Plan Suite at a Blackhawks Game:
Stop climbing over the jersey-dressed masses and slipping in nacho cheese just to get to your seat. For a cool $30,000, you can rent an 80-person suite for a Chicago Blackhawk's regular season game. Friends, colleagues, the normal family members, and you, all enjoying an evening of dudes on ice. Can't come up with 80 compatriots? We call that breathing room. Relax, imbibe, and enjoy live hockey action in luxury. United Center, 1901 West Madison Street (at Damen Avenue); 312-455-4500 .
Rent a luxury yacht on Lake Michigan:
House parties are tired, it's time to take to the sea! Rent a luxury yacht for a good time on Lake Michigan, and earn your stripes as a true baller. Starting at $2,100 for a three hour tour (sorry, we had to), entertain up to 120 people you actually like on a seafaring beauty. Bar and catering packages are available too, at an extra cost. Of course.
CRUISE
Take a helicopter tour of Chicago:
If you want to take in your fair city like a superstar, take to the sky. At $750 an hour, helicopter tours are the perfect way to get your kicks while you learn a little somethin' about the town we love. Here's the best part: there's no traffic in the air! Just you, Chicago, and those spinning blades of fury. Beware, in the summer, helicopters fly with the doors off.
Rent a Ferrari F430 Coupe F1:
What goes from 0-60 in four seconds or less? Your ride for the weekend, that's what. The Ferrari F430 Coupe F1 (say that five times fast) starts at $1,499 a day, but with all that power and beauty a gas pedal away, it's a steal. Leave your work worries and relationship status back in Chicago for the weekend, and hit the freeway. How far do you want to go?
GET GORGEOUS
Get a photo shoot at Vavoom Pinups:
There is nobody prettier than you, and Vavoom Pinups will prove it. Immortalize yourself in true '40s style with a portrait that's just the right amount of camp and vamp. For $400, you'll be fully styled for your four-outfit shoot, plus you'll have an editing and retouching meeting with your photog (this is way better than untagging yourself on Facebook). One complimentary 8x10 print is included, additional prints are extra. You can even try your hand at a boudoir photo, for a small fee. Vavoom Pinups, 2239 North Kimball Avenue (at Belden Street); 773-726-1109 .
Hire your own glam squad from Starlight Chicago:
We're all beauty experts in our own right, but if the event is so special that your nervous shakes prevent you from properly applying eyeliner, hire the pros. For $2,800, you and your pals can hire Starlight Chicago to give you some glam. Hair, makeup, the works. You'll walk out the door camera-ready and confident. Can't decide what to wear? Head immediately to Refinery29 for style advice (we got it in spades!). And our love don't cost a thing.
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