Paid $0 for this oasis in Chicago
We paid nothing for 3 nights of downtown Chicago hotels. 2 nights were covered through points, and the other night was reimbursed through an expense account.

Here’s what we recommend to get a great night at a Chicago hotel.

Priceline - Name your own price can realistically save 50% on a Chicago hotel. They have a Name Your Own Price program where you indicate how much you are willing to pay, the area (for downtown Chicago, choose Area 7 or 8), and what star hotel you would like to stay at. By choosing areas 7 or 8, you ensure walking distances to most of the Chicago CityPASS attractions. Before you bid, check out the forums biddingfortravel.com and betterbidding.com. The Hyatt Regency Chicago in area 7 is an ENORMOUS property that typically has rooms on Priceline. That’s where we stayed.  This allowed us to stretch our travels stipend further since we saved so much money on a room.

Airbnb.com – Locals rent out spare rooms with this site. You can see photos of the rooms, and read reviews from other travelers. If you don’t mind the personal touch it can be a great way to stay in Chicago for cheap. We nearly stayed for $30 a night with Annie on Airbnb. She is very polite and has rave reviews. The only reason we didn’t stay with her was we got approved for a travel stipend and decided to stay closer downtown.

HomeExchange.comYou’d be surprised the interesting people who live in Chicago willing to swap houses with you. I found many downtown Chicago highrise condos listed for swaps. After you undergo a background check, you are free to arrange swaps with travelers all over the world. Including in Chicago!  You have unlimited access to these swaps. We swapped with a retired couple from San Francisco and had a great experience.  They even fed our cat! We recommend this especially if you would like to do some long-term traveling. Did I mention you can swap as much as you like?!

The registration fee is $120 for a full year. That's like one night in a hotel. If you go month to month it is $9.95. However, you can shave 30% off by using code dealshe72010.  A special little promo just for Our Cheap Chicago Vacation Readers.  You're welcome.