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Accommodations

Airbnb
local; flexible
Airbnb is a great option if you're looking for something more affordable than a hotel that is located in a cute urban neighborhood (vs. downtown). Most reservations have no-penalty cancellations.
Here are some neighborhoods we love:
Ukrainian Village
Logan Square
Andersonville
Wicker Park

Hotels
familiar; downtown
Hotels are a great option if you're looking for a more familiar experience and want to stay downtown. If you want to be surrounded by skyscrapers and great architecture, this is for you.
Here are some affordable, highly rated hotels:
Hampton Inn & Suites Chicago-Downtown
Fairfield Inn & Suites by Marriott River North
Acme Hotel Company
Hyatt Place Chicago Downtown/the Loop


Vrbo
groups; families
Similar to Airbnb, Vrbo is better for families and groups. These can be a bit more sparse than Airbnbs, but are similarly affordable.
Here are some family-friendly neighborhoods:
Lincoln Park
Logan Square
Lincoln Square
Edgewater
Hostels
affordable; central
Hostels in the city offer a more affordable stay than hotels, but often with less privacy. Many are located downtown, offering similar access to architecture and experiences located in the city center.
Here are some highly rated hostels downtown:
Freehand Chicago
HI Chicago
Here are some highly rated hostels in other areas:
Wrigley Hostel
Chicago Parthenon Hostel

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