Planning before a trip can make all the difference between a fantastic vacation and one that is more frustrating than fun. It’s not that you need to schedule every minute of every day, but knowing your options before you go saves you time once you’re there and greatly minimizes occurrences of conversations such as:
her: So, what do you feel like doing today?
him: I don’t know. What do you want to do?
her: I don’t know. Any ideas?
him: Nope. What sounds good to you?
both: continue ad nauseum
This multi-part guide will help if you’re planning a trip to Chicago. If you’re not going to Chicago, I recommend a change of plans. It’s a great place to visit.
To begin with, you’ll need a place to sleep. Chicago is a popular city for conventions, and the larger ones can significantly impact hotel room demands and therefore prices. Before you make set plans, check a website such as Choose Chicago’s Convention and Events Calendar to see what’s happening during the dates you’re considering. If you see a large event like Lollapalooza, or a convention (or combination of conventions) with 20,000 or more people, you may find higher hotel prices. Another option is just to search hotel prices for a number of dates on a site like Kayak. You’ll quickly see which dates have higher than normal pricing.
Most visitors to Chicago, especially first-time visitors, prefer staying in Chicago’s central business area, comprised of neighborhoods such as the Magnificent Mile (Michigan Avenue north of the river), River North (north of the river between the river’s north branch and roughly State Street) and the Loop (south of the river, north of Congress Pkwy, between Grant Park to the east and Wacker to the west). There are also some hotels in the Lincoln Park area, and bed & breakfasts in other neighborhoods. In addition, to save money, some visitors prefer to stay in the suburbs and take the train into the city.
The map below highlights 71 hotels in central Chicago. If you’d like to see a list of the hotels by name, click on “view larger map” at the bottom of the map. On that map you can click the balloon by any hotel’s name and it will be centered on the map, so you can easily find the location of any hotel you’re interested in. Much of this map was created by hand, so if you find any mistakes, please send me an email. Feel free to ask questions about hotels or the hotel map in the comments, and I’ll answer if I can.
There are often great savings to be found on Chicago hotels. The first site I check when planning a trip is TravelZoo. They list great hotel bargains when they find them, but you often won’t find anything for a stay more than a couple months away. In addition, both Priceline and Hotwire can be great for finding bargain Chicago hotel rooms. For help with both “blind” hotel sites, check Better Bidding. In a nutshell, Priceline is only good if you’re willing to live with one bed in a room for two people. Hotwire allows you to specify more people in a room, but I’ve typically found the prices to be slightly higher than what I can get bidding on Priceline. Still, it’s worth a check to see if anything wonderful is available.