chgoeditor

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.