Date: 201406
Local time of day: 1801-2400
Location: MDW.Airport, IL
Flight conditions: Mixed
Light: Night
Aircraft: Large Transport; Low Wing; 2 Turbojet Eng
Operator: Air Carrier
Operating under: Part 121
Flight plan: IFR
Mission: Passenger
Flight phase: Initial Approach
Airspace: Class C MDW
ATC / advisory: TRACON C90
Reporter organization: Air Carrier
Reporter function: First Officer
Human factors: Workload; Distraction; Communication Breakdown; Situational Awareness
Second reporter function: Captain
Anomaly: ATC Issue All Types; Deviation / Discrepancy - Procedural Published Material / Policy; Inflight Event / Encounter Weather / Turbulence
Detector: Person Flight Crew
When detected: In-flight
Result: Flight Crew Took Evasive Action
Contributing factors: Weather; Environment - Non Weather Related; Aircraft; Company Policy; Procedure
Primary problem: Ambiguous

Narrative: During arrival; we were told to expect vectors to the visual approach to MDW 22L. Per the cover page of the weather packet; we expected to follow the ground track of the RNAV 22L to comply with ATC. INSTEAD we never had to fly that and we were given radar vectors. Both the Captain and I noticed a cloud layer forming at approximately 3;000 just around the lake on our easterly downwind vector. The Captain advised ATC of the layer. We were then given a heading of due north 360 degrees. We were still IMC. ATC then descended us to 2;500 FT MSL as he also turned us first to 310 and then as we broke out of the layer of clouds at approximately 2;700 FT MSL. We had a great view of the tall downtown buildings; etc. My Captain was about to say something about needing a turn as we were issued a 270 heading that wasn't going to be tight enough. Again about to say something; ATC; without any real urgency; issued a 220 heading. We never received any GPWS caution/warnings; however; this was not a comfortable situation to be in at night in an older model aircraft being vectored around for the visual approach with a ragged cloud formation northeast of the airport. We did call the airport shortly after the Controller issued the 220 heading. We were too busy making sure that we were clear of the downtown structures. We continued the visual approach; maintained all stabilized approach criteria; and landed safely. I strongly recommend prohibiting all older model aircraft (non-RNAV equipped aircraft) from this particular visual; whether under radar vectors to final; or utilizing RNAV ground track (RNAV 22L Y) at night. It seemed to us that there is simply not enough situational awareness for ATC to be 'threading the needle' around downtown buildings. It is better to fly the ILS 31C; circle to land 22L; versus the radar vector to final; if the ceiling are below 4;000 FT to 5;000 FT.


Second narrative: During the descent; ATC vectored us on heading 220 and; just as we broke out of the clouds; we saw downtown and then turned aggressively away. We felt too close to downtown. Remainder of approach and landing uneventful.


Synopsis: An Air Carrier crew on vectors for a MDW Runway 22L visual questioned their ability to remain clear of obstacles in an older technology aircraft while flying IMC over downtown Chicago a 2;500 FT.