*Help* GF Bday on Valentines Day
 

Hello Friends,
My girlfriend turns 21 on February 14th AKA valentines day. I need help planning on where to go and what to do. The last time we celebrated her birthday together I tried to plan a romantic night filled with things she loves. I took her to get Ginos Deepdish, a horse carriage ride from the mag mile to navy pier and back, Ice skating at millennium park, and I tried to get a hotel room at La Quinta Inn, but when we checked in they wouldn't let me as you have to be 21 in Cook Co. to get a room.

Now that I am already 21 and she is turning 21 I'd like to do something for her again. Any suggestions would be helpful, so thank you. I'd like to spend roughly $100-150 as I am on a college budget, but give me all ideas :D

Accommodations: she has a apartment in Lincoln Park so we could totally stay there (on her twin bed though :td: :( ) or I could pay for a hotel/Airbnb in the city. I see that the "W City Center" is $94/night but I don't see too many good reviews. I see that there is a "Hyatt Place Downtown" for $170/night that I can book with Points+Cash for 6k Hyatt Points and $75. This would be nice because of the location and the breakfast.

Dining: The first thing that pops in mind is Dave and Busters. Not because I am a cheap ......., but because I think she would genuinely enjoy it there since we have food, games, and drinks. The other options I was thinking was to take her out on the Odyssey at Navy Pier or go to the Signature Lounge, but if I remember correctly they cost a pretty penny on valentines day. Maybe go to the Signature Lounge and get a drink at least. Her palate is not too sophisticated so we do not need to go anywhere too fancy since she won't appreciate the food and say how she is still hungry.

Extra Curricular: I drawing blanks here. Sure we could do the same thing that we did for her 19th and go ice skating and get on a horse carriage ride, but I want to make it special and unique. Maybe some cool places where we can grab a drink since shes 21. It might still be very cold out so romantic walks might be a little limited. Anything here is appreciated.

*TL;DR* Below

Accommodations: What hotel/Airbnb do I stay at?
Dining: Where do we go to eat and drink?
Events: What else should we do that night?

Accommodations:
Dining:
Events:

Do you want to stay the night of the 13th or 14th? (The 13th will be cheaper in many aspects, especially for food, so something to consider.) I see plenty of options on Hotwire for under $100/night all-in -- check there and on Priceline, and check betterbidding to figure out which hotel you're likely to get.

Does she have any favorite styles of food? There are so many options it's impossible to narrow down without a little more guidance.

As far as activities, have you thought about going to a comedy club or a blues club? Chicago has world-class options for both, and they tend to be relatively inexpensive, especially with student discounts. A wine bar might also be a romantic option for a cold evening. If you don't know a lot about wine, you can order a flight and have the server explain to you what you're tasting. I enjoy the ambiance at both D.O.C. Wine Bar and The Twisted Vine, and I believe flights are under $20 at both.

I am debating if I should stay the 13th or 14th. I have a couple things that make the 13th hard in my head. My mothers birthday is the 12th (I know, my luck) and also if I did this on the 13th my GF wouldn't be 21 yet so it be hard to do the bars. I like the comedy club Idea she'd love that. Also would try the wine tastings, thanks for the recommendations.

In terms of food that she likes its more like pasta, pizza, salmon, russian/european, American style food. Anything basically in those categories. Hope that helped

Nando's Peri-Peri isn't exactly "American", but it is pretty straightforward, delicious chicken that won't break the bank. They've got a few locations scattered around the city depending on what your plans are.

If you want more ethnic Eastern Europe, check out places like Old Lviv in the Ukrainian Village.

Cheap pasta/pizza can be had on Taylor St by UIC.

Given your limited budget, I'm going to suggest you take a different approach. I think you need to get creative and stop thinking of this as birthday + Valentine's Day and don't feel the need to check every box of what you should do on Valentine's Day and what you should do on her birthday.

First, skip the Odyssey, Signature Room and hotel. She lives here, and the Odyssey and Signature Room are overpriced tourist activities. A hotel will blow almost your entire budget.

I'm not sure about Dave & Busters, but most restaurants jack up their prices and serve fixed price menus. It's not worth it, instead I'd suggest:

* Cook her a special dinner. If you don't know how to cook, you have 2.5 months. Practice before hand. Make something delicious with reasonably priced ingredients. Roast cornish game hens or roast pork loin with risotto and a roasted veggie would work. I love a raspberry & dark chocolate semifreddo for an easy to make dessert that's sure to impress, but it's tough to do if you're only arriving in Chicago that day. Get a nice bottle of cava, which shouldn't cost more than $10.

* After dinner, go to a bar or Dave and Busters. Lincoln Park has dozens, and the JParker on the top of the Hotel Lincoln has a fantastic view (and should be less crowded than the Signature Room). If it's warm enough, walk from there to bars on either the Lincoln Ave. strip or in Old Town.

* Forget about her twin bed. Grab some blankets and make a nest for two on the floor.

* If you must splurge on flowers, avoid red roses. Florists are worse than restaurants on Valentine's Day, and crank out a lot of junk at inflated prices. Go to Trader Joe's and buy her an orchid in bloom (<$10) or find a local florist to sell you a couple calla lilies wrapped in ribbon. If necessary, go to a thrift store or ask your mom for a vase -- most women have zillions and it's stupid to buy one from a florist. If roses are a must, order them from Costco to arrive earlier in the week.

Nearly every decent restaurant in Chicago will have a fixed menu with a jacked up price on Valentine's Day. Places like Dave & Busters are probably the exception.

The "cook a meal" option is a good one. Alternatively, do a little detective work and find out what bars are walking distance from her apartment. Most places in Lincoln Park (I live here) are more pub style, with many having decent menus. It might be fun just to go somewhere local as her first night legally in a bar, and able to enjoy a beer or wine with dinner. There are also bars around that have board games, if you're into that at all. Guthrie's in Lakeview comes to mind. Or find a bar with a fireplace and a couch and cozy up for a few drinks...Monkey's Paw in Lincoln Park (they also have good food), I'm sure there are a few others in the area...Google bars with fireplaces.

Definitely skip the touristy options like the Signature Room.

See if the Bulls or Blackhawks are playing that night, if that's something she'd like. Maybe visit the Art Institute during the day?

The thing about Chicago in February is that we all mainly hibernate for that month. So it's difficult to think of a lot of activities that don't result in someone losing fingers or toes.

If you're looking for fireplaces, Duke of Perth comes to mind. Cozy, cheap, and relatively decent food.

Hidden Shamrock recently took out their fireplace and (I think) their board games, but seriously upped their food game.

Prost might be a good option too -- good food, and what better way to celebrate a 21st birthday than with a liter ("maß") of beer? It might not be as romantic, though.