So, in front of me right now is the somewhat daunting task of planning a little mini-getaway for my sweetheart and me. We decided to go to Chicago because we wanted it to feel like we were truly treating ourselves to something special and vacation-like, but without going too far from home. We're still hoping to stay on budget since we are still on the Total Money Makeover, so it's all about keeping it on the cheap. Of course, the biggest expense will be our hotel, so here's where we're at so far on that. Our first step in keeping this trip on budget is:
Book a hotel near the airport and take the train downtown.
Sounds simple enough, right? Where we save money on the crazy prices of a downtown hotel room and outrageous parking fees, we can have more left to spend on attractions and dining. We're travelling on weekdays to try to keep costs down even more. However, this is proving to be a bit more difficult than I originally thought. Here are our options so far:

Pros - Two blocks from the Rosemont "L" stop, Pretty good reviews on Trip Advisor, 3 1/2 star rating, Counts toward Evan's United Miles
Cons - Parking costs $16-$20 per day for a city-run parking ramp, No free Internet in the room ($11.95 per day!)
This hotel looks nice enough, but after paying for parking the bargain begins to sour a bit. I also don't like the idea of having to go to one of the two computers in their "business center" to use the Internet.
Hilton Rosemont / Chicago O'Hare
Price - $79 per night (discounted)
Pros - Two blocks from the Rosemont "L" stop, 3 1/2 star rating, Counts toward Evan's United Miles
Cons - Only 7 reviews on Trip Advisor and the consensus was "okay," No free Internet in rooms and "surcharge" remains a mystery, Parking is $18 per day
Same issues as with the Doubletree, but this hotel seems to be catered even more to the business traveler. The rooms do look really nice. Parking is actually at the hotel, rather than a city lot.
Price - $39.50 per night (discounted)
Pros - Free Internet, Free Parking, CHEAP, Good reviews on Trip Advisor
Cons - 20+ minute drive to nearest "L" stop, Would need to pay to park at Rosemont train station, Not much nearby for dining choices, Location is hard to find.
I'm not sure if the cheap price tag is enough to lure me to stay this far away from the city, which is our main reason for choosing this vacation. Between having to drive into Rosemont and then drive back to the hotel after the train ride out of the city, the hour long commute just doesn't seem worth it.
Price - Starts at $116 per night (no super-secret discount for us here!)
Pros - Free parking, Free Internet, Complimentary shuttle service to the "L" stop, Excellent reviews on Trip Advisor, Counts for Evan's United Miles, Rooms look awesome!
Cons - Price.
This would be the perfect hotel for us, if only we could get a cheaper price. Since we can't....we keep looking!
Holiday Inn O'Hare
Price - Starts at $95 per night (no discount)
Pros - Free parking and Internet, Complimentary shuttle to the Cumberland "L" stop just across the street, Counts for Evan's United Miles
Cons - 3 stars, No "fancy" amenities
I like that this is a more budget-friendly hotel. Even after being able to score the insider deal on the other "fancier" hotels, this one ends up coming out ahead in the value department because of the free Internet and parking. Unless something amazing comes out of nowhere, this might be our winner!
Holiday Inn O'Hare
Price - Starts at $95 per night (no discount)
Pros - Free parking and Internet, Complimentary shuttle to the Cumberland "L" stop just across the street, Counts for Evan's United Miles
Cons - 3 stars, No "fancy" amenities
I like that this is a more budget-friendly hotel. Even after being able to score the insider deal on the other "fancier" hotels, this one ends up coming out ahead in the value department because of the free Internet and parking. Unless something amazing comes out of nowhere, this might be our winner!
Choosing a hotel is proving to be way more difficult than I thought, even with the help of a discount possibility. I've thought about doing the whole "Name Your Price" thing on Priceline, but then you just get to pick a region and you have no idea what hotel you'll actually end up at. I don't really like that idea very much.
Anyone have any suggestions or recommendations for where to stay? How about what to do once we're actually in the city? I'm definitely going to do a post on what to do and where to eat so feel free to suggest away!
