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I think a few photos outside might be ok, but make sure the bridal party is dressed for the occasion (coats, boots, etc). Same goes for you. Chicago winters can be brutal.
As for locations, many of the hotels around Rosemont and the Airport (ie. Hyatt) have beautiful interiors for photos. It's one idea. Even the airport might be a great unusual place for photos that are accessible without needing a boarding pass.
Oooo, the Berger Park/Downey Mansion is really pretty! It's on this website along with a ton of other places/options run by the park district......
http://www.cpdit01.com/resources/permits.special-event-venues/
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Would you recommend photos outside or is it to cold for the bridal party? Also does anyone know any good spots for photos on the NW side of Chicago? We have about 2 hours between the church on the NW side and the reception in Rosemont.
(Jefferson Park, Norwood Park, Edgebrook, Niles, Park Ridge, Rosemont would all be OK and places nearby)