Late night train from Haneda

I will travelling to Tokyo again with my family in this October. My flight will arrive Haneda at 22.30, this is few things i would want to know:-

1. will i be able to catch up train from haneda to shinagawa then to Ikebukuro?

2. I was wondering that i can't catch the last train to Ikebukuro, how long will take for the immigration?

3. Is there any option transportation in case i miss up the last train.

Thanks in advance.

My flight will arrive Haneda at 22.30

Then, usually you can take the last connections of trains to JR Ikebukuro Station.
If your flight and/or immigration procedure happen(s) to be delayed much, you may miss the last connections.

Have you confirmed which exit or gate of which station is good for your Ikebukuro hotel?
JR-East, Tokyo Metro (subway), Seibu Railway and Tobu Railway have Ikebukuro Stations, which make a big railroad terminal.
The last connections of trains to JR Ikebukuro Station are around 23:55.
http://www.jreast.co.jp/e/stations/e108.html
Some hotels in Ikebukuro area are located a little away from the Ikebukuro terminal and rather near subway Higashi-ikebukuro Station of Tokyo Metro.
The last connections of trains to subway Higashi-ikebukuro Station are around 23:30.
http://www.tokyometro.jp/station/higashi-ikebukuro/yardmap/images/yard...
A one-way railroad trip from Haneda Airport International Terminal Station to Ikebukuro Station or Higashi-ikebukuro Station usually needs less than 1000 yen per adult and about 1 hour.

For a few hotels in Ikebukuro area, a limousine bus may be the best option. The last departure is scheduled at 23:25. The one-way bus fare is 1230 yen per adult.
http://www.limousinebus.co.jp/en/platform_searches/index/4/30
http://www.limousinebus.co.jp/en/platform_searches/index/4/31

Note
: If you come on the 18th or a later day of October 2014, timetables for trains of Haneda Airport accesses may be revised by that time.

Is there any option transportation in case i miss up the last train.

At least two limousine buses are scheduled to depart at 00:00 / 00:20 from Haneda Airport International Terminal in your direction.
One is departing from Bus Stop No. 2 and arriving to Ikebukuro Station East Exit Bus Terminal Bus Stop No. 1.
Another is departing from Bus Stop No. 3 and arriving to Shinjuku (Highway) Bus Terminal Bus Stop No. 24.
The one-way bus fare is 2000 yen per adult.
http://www.limousinebus.co.jp/en/platform_searches/index/4/211
http://www.limousinebus.co.jp/en/platform_searches/index/4/214
: If you can have a seat in an Ikebukuro-bound bus, you will not need to take a Shinjuku-bound bus.
: The bus stop in Shinjuku is described as Shinjuku Station West Exit in the webpage, but actually JR Shinjuku Station is a little away from it.
: If a taxi runs smoothly after the midnight from near the bus stop in Shinjuku to JR Ikebukuro Station or subway Higashi-ikebukuro Station, it may need about 2500 yen per car and about 15 minutes.

Connections of trains
(1) Via Monorail Hamamatsucho Sta.
: 750 yen per adult, about 1 hour for (1A).
: 830 yen per adult, about 1 hour for (1B).
Haneda Airport International Terminal Sta.
| [Tokyo Monorail: 490 yen, about 15 min.]
Monorail Hamamatsucho Sta.
--transfer (for about 10 min.) via monorail exit gate and JR entrance gate--
(1A)
Hamamatsucho Sta.: Track 2
| [JR Yamanote Linefs inner loop: 260 yen, about 30 min.]
Ikebukuro Sta.
(1B)
Hamamatsucho Sta.: Track 2
| [JR Yamanote Linefs inner loop: 140 yen, 5 min. or less]
Yurakucho Sta.
--transfer (for about 10 min.) via JR exit gate and subway entrance gate--
Yurakucho Sta.: Track 2
| [Tokyo Metro (subway) Yurakucho Line: 200 yen, about 15 min.]
Higashi-ikebukuro Sta.
(2) Via Shinagawa Sta.
: 670 yen per adult, about 1 hour for (2A).
: 770 yen per adult, about 1 hour for (2B).
Haneda Airport International Terminal Sta.
| [Keikyu: 410 yen, about 10 to 20 min.]
Shinagawa Sta.
--transfer (for about 10 min.) via Keikyu-JR transfer gate--
(2A)
Shinagawa Sta.: Track 2
| [JR Yamanote Linefs outer loop: 260 yen, about 30 min.]
Ikebukuro Sta.
(2B)
Shinagawa Sta.: Track 1
| [JR Yamanote Linefs inner loop: 160 yen, about 10 min.]
--transfer (for about 10 min.) via JR exit gate and subway entrance gate--
Yurakucho Sta.: Track 2
| [Tokyo Metro (subway) Yurakucho Line: 200 yen, about 15 min.]
Higashi-ikebukuro Sta.

"Yurakucho Sta." (of JR) is missing regarding Option (2B).

When you take the route via Shinagawa Station but the earliest Keikyu train is not destined to Shinagawa, please feel free to ask a Keikyu station attendant which train you should take to Shinagawa. Keikyu trains leaving HND run in plural directions.

If you head to a hotel near subway Higashi-ikebukuro Station, you may encounter a staircase in JR Yurakucho Station. You might hope to alternatively reach JR Ikebukuro Station first by rail and catch a taxi.

I suppose that the Ikebukuro railroad terminal is rather friendly to first-time visitors with many signs (including some in English), but I also have impression that it is sometimes difficult to find a correct route around Ikebukuro Stations. I recommend you check your route well in advance if you plan to walk from JR Ikebukuro Station.

As my one advise,AirAisa airplane sometimes arrive at further place from main Haneda terminal.
You may need to ride a airport bus to terminal from airplane.

It means that you must consider an extra wasting time.
Also you have to consider a extra time to pick up your luggage if you have a suitcase.

I have a experience to miss last train....

Anyway, please consider worst scenario.